diff --git a/.gitignore b/.gitignore
index 563cf1be4..7ae66eed5 100644
--- a/.gitignore
+++ b/.gitignore
@@ -34,3 +34,6 @@ node_modules/
 
 # Firebase credentials
 ohq-firebase-*.json
+
+# Env variables
+.env
\ No newline at end of file
diff --git a/backend/.gitignore b/backend/.gitignore
new file mode 100644
index 000000000..90624f3e5
--- /dev/null
+++ b/backend/.gitignore
@@ -0,0 +1 @@
+question_files
\ No newline at end of file
diff --git a/backend/Pipfile b/backend/Pipfile
index 73707c030..e01619b61 100644
--- a/backend/Pipfile
+++ b/backend/Pipfile
@@ -5,7 +5,7 @@ verify_ssl = true
 
 [dev-packages]
 codecov = "*"
-black = "==19.10b0"
+black = "==22.3.0"
 unittest-xml-reporting = "*"
 flake8 = "*"
 flake8-absolute-import = "*"
@@ -22,7 +22,7 @@ djangorestframework = "*"
 psycopg2 = "*"
 sentry-sdk = "*"
 django = "==3.1.7"
-django-cors-headers = "*"
+django-cors-headers = "==3.11.0"
 pyyaml = "*"
 uritemplate = "*"
 uwsgi = "*"
@@ -44,6 +44,8 @@ gunicorn = "*"
 django-scheduler = "*"
 typing-extensions = "*"
 drf-excel = "*"
+boto3 = "*"
+django-storages = "*"
 
 [requires]
 python_version = "3"
diff --git a/backend/Pipfile.lock b/backend/Pipfile.lock
index c3d01fed6..cf7186788 100644
--- a/backend/Pipfile.lock
+++ b/backend/Pipfile.lock
@@ -1,7 +1,7 @@
 {
     "_meta": {
         "hash": {
-            "sha256": "1284b5f2733885bd690e9557203ed07c65e674a13d4a23ccad77534e0ded9b9a"
+            "sha256": "e062f4bcb4cf2109d98e875f8f7e25b4296bc3f26b87388905e9fadcc16489db"
         },
         "pipfile-spec": 6,
         "requires": {
@@ -16,59 +16,52 @@
         ]
     },
     "default": {
-        "aioredis": {
-            "hashes": [
-                "sha256:15f8af30b044c771aee6787e5ec24694c048184c7b9e54c3b60c750a4b93273a",
-                "sha256:b61808d7e97b7cd5a92ed574937a079c9387fdadd22bfbfa7ad2fd319ecc26e3"
-            ],
-            "version": "==1.3.1"
-        },
         "amqp": {
             "hashes": [
-                "sha256:446b3e8a8ebc2ceafd424ffcaab1c353830d48161256578ed7a65448e601ebed",
-                "sha256:a575f4fa659a2290dc369b000cff5fea5c6be05fe3f2d5e511bcf56c7881c3ef"
+                "sha256:2c1b13fecc0893e946c65cbd5f36427861cffa4ea2201d8f6fca22e2a373b5e2",
+                "sha256:6f0956d2c23d8fa6e7691934d8c3930eadb44972cbbd1a7ae3a520f735d43359"
             ],
-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==5.1.0"
+            "markers": "python_version >= '3.6'",
+            "version": "==5.1.1"
         },
         "anyio": {
             "hashes": [
-                "sha256:a0aeffe2fb1fdf374a8e4b471444f0f3ac4fb9f5a5b542b48824475e0042a5a6",
-                "sha256:b5fa16c5ff93fa1046f2eeb5bbff2dad4d3514d6cda61d02816dba34fa8c3c2e"
+                "sha256:413adf95f93886e442aea925f3ee43baa5a765a64a0f52c6081894f9992fdd0b",
+                "sha256:cb29b9c70620506a9a8f87a309591713446953302d7d995344d0d7c6c0c9a7be"
             ],
             "markers": "python_full_version >= '3.6.2'",
-            "version": "==3.5.0"
+            "version": "==3.6.1"
         },
         "asgiref": {
             "hashes": [
-                "sha256:2f8abc20f7248433085eda803936d98992f1343ddb022065779f37c5da0181d0",
-                "sha256:88d59c13d634dcffe0510be048210188edd79aeccb6a6c9028cdad6f31d730a9"
+                "sha256:1d2880b792ae8757289136f1db2b7b99100ce959b2aa57fd69dab783d05afac4",
+                "sha256:4a29362a6acebe09bf1d6640db38c1dc3d9217c68e6f9f6204d72667fc19a424"
             ],
             "markers": "python_version >= '3.7'",
-            "version": "==3.5.0"
+            "version": "==3.5.2"
         },
         "async-timeout": {
             "hashes": [
                 "sha256:2163e1640ddb52b7a8c80d0a67a08587e5d245cc9c553a74a847056bc2976b15",
                 "sha256:8ca1e4fcf50d07413d66d1a5e416e42cfdf5851c981d679a09851a6853383b3c"
             ],
-            "markers": "python_full_version >= '3.6.0'",
+            "markers": "python_version >= '3.6'",
             "version": "==4.0.2"
         },
         "attrs": {
             "hashes": [
-                "sha256:2d27e3784d7a565d36ab851fe94887c5eccd6a463168875832a1be79c82828b4",
-                "sha256:626ba8234211db98e869df76230a137c4c40a12d72445c45d5f5b716f076e2fd"
+                "sha256:29adc2665447e5191d0e7c568fde78b21f9672d344281d0c6e1ab085429b22b6",
+                "sha256:86efa402f67bf2df34f51a335487cf46b1ec130d02b8d39fd248abfd30da551c"
             ],
-            "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3, 3.4'",
-            "version": "==21.4.0"
+            "markers": "python_version >= '3.5'",
+            "version": "==22.1.0"
         },
         "autobahn": {
             "hashes": [
-                "sha256:60e1f4c602aacd052ffe3d46ae40b6b75f8286b3c46922c213b523162e58c17e"
+                "sha256:8b462ea2e6aad6b4dc0ed45fb800b6cbfeb0325e7fe6983907f122f2be4a1fe9"
             ],
             "markers": "python_version >= '3.7'",
-            "version": "==22.2.2"
+            "version": "==22.7.1"
         },
         "automat": {
             "hashes": [
@@ -79,11 +72,11 @@
         },
         "beautifulsoup4": {
             "hashes": [
-                "sha256:9a315ce70049920ea4572a4055bc4bd700c940521d36fc858205ad4fcde149bf",
-                "sha256:c23ad23c521d818955a4151a67d81580319d4bf548d3d49f4223ae041ff98891"
+                "sha256:58d5c3d29f5a36ffeb94f02f0d786cd53014cf9b3b3951d42e0080d8a9498d30",
+                "sha256:ad9aa55b65ef2808eb405f46cf74df7fcb7044d5cbc26487f96eb2ef2e436693"
             ],
-            "markers": "python_version >= '3.1'",
-            "version": "==4.10.0"
+            "markers": "python_version >= '3.6'",
+            "version": "==4.11.1"
         },
         "billiard": {
             "hashes": [
@@ -92,83 +85,106 @@
             ],
             "version": "==3.6.4.0"
         },
-        "cached-property": {
+        "boto3": {
+            "hashes": [
+                "sha256:3225366014949039e6687387242e73f237f0fee0a9b7c20461894f1ee40686b8",
+                "sha256:b295640bc1be637f8f7c8c8fca70781048d6397196109e59f20541824fab4b67"
+            ],
+            "index": "pypi",
+            "version": "==1.24.91"
+        },
+        "botocore": {
             "hashes": [
-                "sha256:9fa5755838eecbb2d234c3aa390bd80fbd3ac6b6869109bfc1b499f7bd89a130",
-                "sha256:df4f613cf7ad9a588cc381aaf4a512d26265ecebd5eb9e1ba12f1319eb85a6a0"
+                "sha256:1d6e97bd8653f732c7078b34aa2bb438e750898957e5a0a74b6c72918bc1d0f7",
+                "sha256:c8fac203a391cc2e4b682877bfce70e723e33c529b35b399a1d574605fbeb1af"
             ],
-            "markers": "python_version < '3.8'",
-            "version": "==1.5.2"
+            "markers": "python_version >= '3.7'",
+            "version": "==1.27.91"
         },
         "celery": {
             "hashes": [
-                "sha256:8aacd02fc23a02760686d63dde1eb0daa9f594e735e73ea8fb15c2ff15cb608c",
-                "sha256:e2cd41667ad97d4f6a2f4672d1c6a6ebada194c619253058b5f23704aaadaa82"
+                "sha256:138420c020cd58d6707e6257b6beda91fd39af7afde5d36c6334d175302c0e14",
+                "sha256:fafbd82934d30f8a004f81e8f7a062e31413a23d444be8ee3326553915958c6d"
             ],
             "index": "pypi",
-            "version": "==5.2.3"
+            "version": "==5.2.7"
         },
         "certifi": {
             "hashes": [
-                "sha256:78884e7c1d4b00ce3cea67b44566851c4343c120abd683433ce934a68ea58872",
-                "sha256:d62a0163eb4c2344ac042ab2bdf75399a71a2d8c7d47eac2e2ee91b9d6339569"
+                "sha256:0d9c601124e5a6ba9712dbc60d9c53c21e34f5f641fe83002317394311bdce14",
+                "sha256:90c1a32f1d68f940488354e36370f6cca89f0f106db09518524c88d6ed83f382"
             ],
-            "version": "==2021.10.8"
+            "markers": "python_version >= '3.6'",
+            "version": "==2022.9.24"
         },
         "cffi": {
             "hashes": [
-                "sha256:00c878c90cb53ccfaae6b8bc18ad05d2036553e6d9d1d9dbcf323bbe83854ca3",
-                "sha256:0104fb5ae2391d46a4cb082abdd5c69ea4eab79d8d44eaaf79f1b1fd806ee4c2",
-                "sha256:06c48159c1abed75c2e721b1715c379fa3200c7784271b3c46df01383b593636",
-                "sha256:0808014eb713677ec1292301ea4c81ad277b6cdf2fdd90fd540af98c0b101d20",
-                "sha256:10dffb601ccfb65262a27233ac273d552ddc4d8ae1bf93b21c94b8511bffe728",
-                "sha256:14cd121ea63ecdae71efa69c15c5543a4b5fbcd0bbe2aad864baca0063cecf27",
-                "sha256:17771976e82e9f94976180f76468546834d22a7cc404b17c22df2a2c81db0c66",
-                "sha256:181dee03b1170ff1969489acf1c26533710231c58f95534e3edac87fff06c443",
-                "sha256:23cfe892bd5dd8941608f93348c0737e369e51c100d03718f108bf1add7bd6d0",
-                "sha256:263cc3d821c4ab2213cbe8cd8b355a7f72a8324577dc865ef98487c1aeee2bc7",
-                "sha256:2756c88cbb94231c7a147402476be2c4df2f6078099a6f4a480d239a8817ae39",
-                "sha256:27c219baf94952ae9d50ec19651a687b826792055353d07648a5695413e0c605",
-                "sha256:2a23af14f408d53d5e6cd4e3d9a24ff9e05906ad574822a10563efcef137979a",
-                "sha256:31fb708d9d7c3f49a60f04cf5b119aeefe5644daba1cd2a0fe389b674fd1de37",
-                "sha256:3415c89f9204ee60cd09b235810be700e993e343a408693e80ce7f6a40108029",
-                "sha256:3773c4d81e6e818df2efbc7dd77325ca0dcb688116050fb2b3011218eda36139",
-                "sha256:3b96a311ac60a3f6be21d2572e46ce67f09abcf4d09344c49274eb9e0bf345fc",
-                "sha256:3f7d084648d77af029acb79a0ff49a0ad7e9d09057a9bf46596dac9514dc07df",
-                "sha256:41d45de54cd277a7878919867c0f08b0cf817605e4eb94093e7516505d3c8d14",
-                "sha256:4238e6dab5d6a8ba812de994bbb0a79bddbdf80994e4ce802b6f6f3142fcc880",
-                "sha256:45db3a33139e9c8f7c09234b5784a5e33d31fd6907800b316decad50af323ff2",
-                "sha256:45e8636704eacc432a206ac7345a5d3d2c62d95a507ec70d62f23cd91770482a",
-                "sha256:4958391dbd6249d7ad855b9ca88fae690783a6be9e86df65865058ed81fc860e",
-                "sha256:4a306fa632e8f0928956a41fa8e1d6243c71e7eb59ffbd165fc0b41e316b2474",
-                "sha256:57e9ac9ccc3101fac9d6014fba037473e4358ef4e89f8e181f8951a2c0162024",
-                "sha256:59888172256cac5629e60e72e86598027aca6bf01fa2465bdb676d37636573e8",
-                "sha256:5e069f72d497312b24fcc02073d70cb989045d1c91cbd53979366077959933e0",
-                "sha256:64d4ec9f448dfe041705426000cc13e34e6e5bb13736e9fd62e34a0b0c41566e",
-                "sha256:6dc2737a3674b3e344847c8686cf29e500584ccad76204efea14f451d4cc669a",
-                "sha256:74fdfdbfdc48d3f47148976f49fab3251e550a8720bebc99bf1483f5bfb5db3e",
-                "sha256:75e4024375654472cc27e91cbe9eaa08567f7fbdf822638be2814ce059f58032",
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-                "sha256:8b6c2ea03845c9f501ed1313e78de148cd3f6cad741a75d43a29b43da27f2e1e",
-                "sha256:91d77d2a782be4274da750752bb1650a97bfd8f291022b379bb8e01c66b4e96b",
-                "sha256:91ec59c33514b7c7559a6acda53bbfe1b283949c34fe7440bcf917f96ac0723e",
-                "sha256:920f0d66a896c2d99f0adbb391f990a84091179542c205fa53ce5787aff87954",
-                "sha256:a5263e363c27b653a90078143adb3d076c1a748ec9ecc78ea2fb916f9b861962",
-                "sha256:abb9a20a72ac4e0fdb50dae135ba5e77880518e742077ced47eb1499e29a443c",
-                "sha256:c2051981a968d7de9dd2d7b87bcb9c939c74a34626a6e2f8181455dd49ed69e4",
-                "sha256:c21c9e3896c23007803a875460fb786118f0cdd4434359577ea25eb556e34c55",
-                "sha256:c2502a1a03b6312837279c8c1bd3ebedf6c12c4228ddbad40912d671ccc8a962",
-                "sha256:d4d692a89c5cf08a8557fdeb329b82e7bf609aadfaed6c0d79f5a449a3c7c023",
-                "sha256:da5db4e883f1ce37f55c667e5c0de439df76ac4cb55964655906306918e7363c",
-                "sha256:e7022a66d9b55e93e1a845d8c9eba2a1bebd4966cd8bfc25d9cd07d515b33fa6",
-                "sha256:ef1f279350da2c586a69d32fc8733092fd32cc8ac95139a00377841f59a3f8d8",
-                "sha256:f54a64f8b0c8ff0b64d18aa76675262e1700f3995182267998c31ae974fbc382",
-                "sha256:f5c7150ad32ba43a07c4479f40241756145a1f03b43480e058cfd862bf5041c7",
-                "sha256:f6f824dc3bce0edab5f427efcfb1d63ee75b6fcb7282900ccaf925be84efb0fc",
-                "sha256:fd8a250edc26254fe5b33be00402e6d287f562b6a5b2152dec302fa15bb3e997",
-                "sha256:ffaa5c925128e29efbde7301d8ecaf35c8c60ffbcd6a1ffd3a552177c8e5e796"
-            ],
-            "version": "==1.15.0"
+                "sha256:00a9ed42e88df81ffae7a8ab6d9356b371399b91dbdf0c3cb1e84c03a13aceb5",
+                "sha256:03425bdae262c76aad70202debd780501fabeaca237cdfddc008987c0e0f59ef",
+                "sha256:04ed324bda3cda42b9b695d51bb7d54b680b9719cfab04227cdd1e04e5de3104",
+                "sha256:0e2642fe3142e4cc4af0799748233ad6da94c62a8bec3a6648bf8ee68b1c7426",
+                "sha256:173379135477dc8cac4bc58f45db08ab45d228b3363adb7af79436135d028405",
+                "sha256:198caafb44239b60e252492445da556afafc7d1e3ab7a1fb3f0584ef6d742375",
+                "sha256:1e74c6b51a9ed6589199c787bf5f9875612ca4a8a0785fb2d4a84429badaf22a",
+                "sha256:2012c72d854c2d03e45d06ae57f40d78e5770d252f195b93f581acf3ba44496e",
+                "sha256:21157295583fe8943475029ed5abdcf71eb3911894724e360acff1d61c1d54bc",
+                "sha256:2470043b93ff09bf8fb1d46d1cb756ce6132c54826661a32d4e4d132e1977adf",
+                "sha256:285d29981935eb726a4399badae8f0ffdff4f5050eaa6d0cfc3f64b857b77185",
+                "sha256:30d78fbc8ebf9c92c9b7823ee18eb92f2e6ef79b45ac84db507f52fbe3ec4497",
+                "sha256:320dab6e7cb2eacdf0e658569d2575c4dad258c0fcc794f46215e1e39f90f2c3",
+                "sha256:33ab79603146aace82c2427da5ca6e58f2b3f2fb5da893ceac0c42218a40be35",
+                "sha256:3548db281cd7d2561c9ad9984681c95f7b0e38881201e157833a2342c30d5e8c",
+                "sha256:3799aecf2e17cf585d977b780ce79ff0dc9b78d799fc694221ce814c2c19db83",
+                "sha256:39d39875251ca8f612b6f33e6b1195af86d1b3e60086068be9cc053aa4376e21",
+                "sha256:3b926aa83d1edb5aa5b427b4053dc420ec295a08e40911296b9eb1b6170f6cca",
+                "sha256:3bcde07039e586f91b45c88f8583ea7cf7a0770df3a1649627bf598332cb6984",
+                "sha256:3d08afd128ddaa624a48cf2b859afef385b720bb4b43df214f85616922e6a5ac",
+                "sha256:3eb6971dcff08619f8d91607cfc726518b6fa2a9eba42856be181c6d0d9515fd",
+                "sha256:40f4774f5a9d4f5e344f31a32b5096977b5d48560c5592e2f3d2c4374bd543ee",
+                "sha256:4289fc34b2f5316fbb762d75362931e351941fa95fa18789191b33fc4cf9504a",
+                "sha256:470c103ae716238bbe698d67ad020e1db9d9dba34fa5a899b5e21577e6d52ed2",
+                "sha256:4f2c9f67e9821cad2e5f480bc8d83b8742896f1242dba247911072d4fa94c192",
+                "sha256:50a74364d85fd319352182ef59c5c790484a336f6db772c1a9231f1c3ed0cbd7",
+                "sha256:54a2db7b78338edd780e7ef7f9f6c442500fb0d41a5a4ea24fff1c929d5af585",
+                "sha256:5635bd9cb9731e6d4a1132a498dd34f764034a8ce60cef4f5319c0541159392f",
+                "sha256:59c0b02d0a6c384d453fece7566d1c7e6b7bae4fc5874ef2ef46d56776d61c9e",
+                "sha256:5d598b938678ebf3c67377cdd45e09d431369c3b1a5b331058c338e201f12b27",
+                "sha256:5df2768244d19ab7f60546d0c7c63ce1581f7af8b5de3eb3004b9b6fc8a9f84b",
+                "sha256:5ef34d190326c3b1f822a5b7a45f6c4535e2f47ed06fec77d3d799c450b2651e",
+                "sha256:6975a3fac6bc83c4a65c9f9fcab9e47019a11d3d2cf7f3c0d03431bf145a941e",
+                "sha256:6c9a799e985904922a4d207a94eae35c78ebae90e128f0c4e521ce339396be9d",
+                "sha256:70df4e3b545a17496c9b3f41f5115e69a4f2e77e94e1d2a8e1070bc0c38c8a3c",
+                "sha256:7473e861101c9e72452f9bf8acb984947aa1661a7704553a9f6e4baa5ba64415",
+                "sha256:8102eaf27e1e448db915d08afa8b41d6c7ca7a04b7d73af6514df10a3e74bd82",
+                "sha256:87c450779d0914f2861b8526e035c5e6da0a3199d8f1add1a665e1cbc6fc6d02",
+                "sha256:8b7ee99e510d7b66cdb6c593f21c043c248537a32e0bedf02e01e9553a172314",
+                "sha256:91fc98adde3d7881af9b59ed0294046f3806221863722ba7d8d120c575314325",
+                "sha256:94411f22c3985acaec6f83c6df553f2dbe17b698cc7f8ae751ff2237d96b9e3c",
+                "sha256:98d85c6a2bef81588d9227dde12db8a7f47f639f4a17c9ae08e773aa9c697bf3",
+                "sha256:9ad5db27f9cabae298d151c85cf2bad1d359a1b9c686a275df03385758e2f914",
+                "sha256:a0b71b1b8fbf2b96e41c4d990244165e2c9be83d54962a9a1d118fd8657d2045",
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+            "version": "==1.15.1"
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         "channels": {
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@@ -180,34 +196,34 @@
         },
         "channels-redis": {
             "hashes": [
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-                "sha256:6e4565b7c11c6bcde5d48556cb83bd043779697ff03811867d2f895aa6170d56"
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-            "version": "==3.4.0"
+            "version": "==4.0.0"
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-                "sha256:6881edbebdb17b39b4eaaa821b438bf6eddffb4468cf344f09f89def34a8b1df"
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-            "markers": "python_version >= '3'",
-            "version": "==2.0.12"
+            "markers": "python_version >= '3.6'",
+            "version": "==2.1.1"
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         "click": {
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-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==8.0.4"
+            "markers": "python_version >= '3.7'",
+            "version": "==8.1.3"
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-            "markers": "python_version < '4' and python_full_version >= '3.6.2'",
+            "markers": "python_full_version >= '3.6.2' and python_full_version < '4.0.0'",
             "version": "==0.3.0"
         },
         "click-plugins": {
@@ -233,29 +249,35 @@
         },
         "cryptography": {
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-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==36.0.2"
+            "markers": "python_version >= '3.6'",
+            "version": "==38.0.1"
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         "daphne": {
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@@ -333,11 +355,11 @@
                 "phonenumbers"
             ],
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-                "sha256:897b902a1654b0eb21f6268498a3359e2c4eb90af9585cb8693af186ede8c5bb",
-                "sha256:b1ff950f90a8911ff323ccf77c8f6fe4299a9f671fa61c8734a6994359f07446"
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-            "version": "==6.1.0"
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@@ -349,19 +371,26 @@
         },
         "django-scheduler": {
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-                "sha256:a14c6320a849187b3cc27c69c00b6575f8f6a6ff7e0fff4f2de3f6179d6d0fdd"
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             "index": "pypi",
-            "version": "==0.9.5"
+            "version": "==0.9.6"
+        },
+        "django-storages": {
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+                "sha256:204a99f218b747c46edbfeeb1310d357f83f90fa6a6024d8d0a3f422570cee84",
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+            ],
+            "index": "pypi",
+            "version": "==1.12.3"
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         "djangorestframework": {
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-                "sha256:24c4bf58ed7e85d1fe4ba250ab2da926d263cd57d64b03e8dcef0ac683f8b1aa"
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-            "version": "==3.13.1"
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@@ -372,11 +401,11 @@
         },
         "drf-excel": {
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-            "version": "==2.1.0"
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@@ -391,7 +420,7 @@
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-            "markers": "python_full_version >= '3.6.0'",
+            "markers": "python_version >= '3.6'",
             "version": "==1.1.0"
         },
         "gunicorn": {
@@ -404,97 +433,57 @@
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@@ -505,33 +494,34 @@
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@@ -543,98 +533,116 @@
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+                "sha256:fcb8a47f43acc113e24e910399376f7277cf8508b27e5b88499f053de6b115a8"
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+            "version": "==1.0.4"
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-                "sha256:6db33440354787f9b7f3a6dbd4febf5d0f93758354060e802f6c06cb493022fe"
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-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==3.2.0"
+            "markers": "python_version >= '3.6'",
+            "version": "==3.2.1"
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         "openpyxl": {
             "hashes": [
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-                "sha256:8f3b11bd896a95468a4ab162fc4fcd260d46157155d1f8bfaabb99d88cfcf79f"
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+                "sha256:e47805627aebcf860edb4edf7987b1309c1b3632f3750538ed962bbcc3bd7449"
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-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==3.0.9"
+            "markers": "python_version >= '3.6'",
+            "version": "==3.0.10"
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         "packaging": {
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                 "sha256:ef103e05f519cdc783ae24ea4e2e0f508a9c99b2d4969652eed6a2e1ea5bd522"
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-            "markers": "python_full_version >= '3.6.0'",
+            "markers": "python_version >= '3.6'",
             "version": "==21.3"
         },
         "phonenumbers": {
             "hashes": [
-                "sha256:94e30f59b2be6c4310a90f3d5da53d49900bdb440484506f3333c694ebb0cdab",
-                "sha256:e3af21c1e33a3dd063cddba3cad653abb8d23c37c62cedee597a3f3ea0f5365c"
+                "sha256:057d1966962fb86b3dc447bfac2c8e25ceed774509e49b180926a13a99910318",
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-            "version": "==8.12.45"
+            "version": "==8.12.57"
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         "prompt-toolkit": {
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-                "sha256:9f1cd16b1e86c2968f2519d7fb31dd9d669916f515612c269d14e9ed52b51650"
+                "sha256:9696f386133df0fc8ca5af4895afe5d78f5fcfe5258111c2a79a1c3e41ffa96d",
+                "sha256:9ada952c9d1787f52ff6d5f3484d0b4df8952787c087edf6a1f7c2cb1ea88148"
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             "markers": "python_full_version >= '3.6.2'",
-            "version": "==3.0.28"
+            "version": "==3.0.31"
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         "psycopg2": {
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-                "sha256:d3ca6421b942f60c008f81a3541e8faf6865a28d5a9b48544b0ee4f40cac7fca"
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+                "sha256:839f9ea8f6098e39966d97fcb8d08548fbc57c523a1e27a1f0609addf40f777c",
+                "sha256:849bd868ae3369932127f0771c08d1109b254f08d48dc42493c3d1b87cb2d308",
+                "sha256:8de6a9fc5f42fa52f559e65120dcd7502394692490c98fed1221acf0819d7797",
+                "sha256:a11946bad3557ca254f17357d5a4ed63bdca45163e7a7d2bfb8e695df069cc3a",
+                "sha256:aa184d551a767ad25df3b8d22a0a62ef2962e0e374c04f6cbd1204947f540d61",
+                "sha256:aafa96f2da0071d6dd0cbb7633406d99f414b40ab0f918c9d9af7df928a1accb",
+                "sha256:c7fa041b4acb913f6968fce10169105af5200f296028251d817ab37847c30184",
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-            "version": "==2.9.3"
+            "version": "==2.9.4"
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         "pyasn1": {
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@@ -682,26 +690,26 @@
         },
         "pyjwt": {
             "hashes": [
-                "sha256:b888b4d56f06f6dcd777210c334e69c737be74755d3e5e9ee3fe67dc18a0ee41",
-                "sha256:e0c4bb8d9f0af0c7f5b1ec4c5036309617d03d56932877f2f7a0beeb5318322f"
+                "sha256:8d82e7087868e94dd8d7d418e5088ce64f7daab4b36db654cbaedb46f9d1ca80",
+                "sha256:e77ab89480905d86998442ac5788f35333fa85f65047a534adc38edf3c88fc3b"
             ],
-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==2.3.0"
+            "markers": "python_version >= '3.7'",
+            "version": "==2.5.0"
         },
         "pyopenssl": {
             "hashes": [
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-                "sha256:ea252b38c87425b64116f808355e8da644ef9b07e429398bfece610f893ee2e0"
+                "sha256:7a83b7b272dd595222d672f5ce29aa030f1fb837630ef229f62e72e395ce8968",
+                "sha256:b28437c9773bb6c6958628cf9c3bebe585de661dba6f63df17111966363dd15e"
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-            "version": "==22.0.0"
+            "version": "==22.1.0"
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         "pyparsing": {
             "hashes": [
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-                "sha256:a6c06a88f252e6c322f65faf8f418b16213b51bdfaece0524c1c1bc30c63c484"
+                "sha256:2b020ecf7d21b687f219b71ecad3631f644a47f01403fa1d1036b0c6416d70fb",
+                "sha256:5026bae9a10eeaefb61dab2f09052b9f4307d44aee4eda64b309723d8d206bbc"
             ],
-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==3.0.7"
+            "markers": "python_full_version >= '3.6.8'",
+            "version": "==3.0.9"
         },
         "python-dateutil": {
             "hashes": [
@@ -713,20 +721,21 @@
         },
         "python-dotenv": {
             "hashes": [
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+                "sha256:1684eb44636dd462b66c3ee016599815514527ad99965de77f43e0944634a7e5",
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-            "version": "==0.19.2"
+            "version": "==0.21.0"
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         "pytz": {
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-                "sha256:e68985985296d9a66a881eb3193b0906246245294a881e7c8afe623866ac6a5c"
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+                "sha256:48ce799d83b6f8aab2020e369b627446696619e79645419610b9facd909b3174"
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-            "version": "==2022.1"
+            "version": "==2022.4"
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         "pyyaml": {
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@@ -738,26 +747,32 @@
                 "sha256:277a0ef2981ca40581a47093e9e2d13b3f1fbbeffae064c1d21bfceba2030287",
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                 "sha256:77f396e6ef4c73fdc33a9157446466f1cff553d979bd00ecb64385760c6babdc",
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                 "sha256:a80a78046a72361de73f8f395f1f1e49f956c6be882eed58505a15f3e430962b",
+                "sha256:afa17f5bc4d1b10afd4466fd3a44dc0e245382deca5b3c353d8b757f9e3ecb8d",
                 "sha256:b3d267842bf12586ba6c734f89d1f5b871df0273157918b0ccefa29deb05c21c",
                 "sha256:b5b9eccad747aabaaffbc6064800670f0c297e52c12754eb1d976c57e4f74dcb",
+                "sha256:bfaef573a63ba8923503d27530362590ff4f576c626d86a9fed95822a8255fd7",
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                 "sha256:d15a181d1ecd0d4270dc32edb46f7cb7733c7c508857278d3d378d14d606db2d",
+                "sha256:d4b0ba9512519522b118090257be113b9468d804b19d63c71dbcf4a48fa32358",
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                 "sha256:daf496c58a8c52083df09b80c860005194014c3698698d1a57cbcfa182142a3a",
+                "sha256:dbad0e9d368bb989f4515da330b88a057617d16b6a8245084f1b05400f24609f",
                 "sha256:e61ceaab6f49fb8bdfaa0f92c4b57bcfbea54c09277b1b4f7ac376bfb7a7c174",
                 "sha256:f84fbc98b019fef2ee9a1cb3ce93e3187a6df0b2538a651bfb890254ba9f90b5"
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@@ -766,19 +781,19 @@
         },
         "redis": {
             "hashes": [
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-                "sha256:1d9a0cdf89fdd93f84261733e24f55a7bbd413a9b219fdaf56e3e728ca9a2306"
+                "sha256:a52d5694c9eb4292770084fa8c863f79367ca19884b329ab574d5cb2036b3e54",
+                "sha256:ddf27071df4adf3821c4f2ca59d67525c3a82e5f268bed97b813cb4fabf87880"
             ],
             "index": "pypi",
-            "version": "==4.1.4"
+            "version": "==4.3.4"
         },
         "requests": {
             "hashes": [
-                "sha256:68d7c56fd5a8999887728ef304a6d12edc7be74f1cfa47714fc8b414525c9a61",
-                "sha256:f22fa1e554c9ddfd16e6e41ac79759e17be9e492b3587efa038054674760e72d"
+                "sha256:7c5599b102feddaa661c826c56ab4fee28bfd17f5abca1ebbe3e7f19d7c97983",
+                "sha256:8fefa2a1a1365bf5520aac41836fbee479da67864514bdb821f31ce07ce65349"
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-            "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3, 3.4, 3.5'",
-            "version": "==2.27.1"
+            "markers": "python_version >= '3.7' and python_full_version < '4.0.0'",
+            "version": "==2.28.1"
         },
         "requests-oauthlib": {
             "hashes": [
@@ -788,13 +803,21 @@
             "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3'",
             "version": "==1.3.1"
         },
+        "s3transfer": {
+            "hashes": [
+                "sha256:06176b74f3a15f61f1b4f25a1fc29a4429040b7647133a463da8fa5bd28d5ecd",
+                "sha256:2ed07d3866f523cc561bf4a00fc5535827981b117dd7876f036b0c1aca42c947"
+            ],
+            "markers": "python_version >= '3.7'",
+            "version": "==0.6.0"
+        },
         "sentry-sdk": {
             "hashes": [
-                "sha256:32af1a57954576709242beb8c373b3dbde346ac6bd616921def29d68846fb8c3",
-                "sha256:38fd16a92b5ef94203db3ece10e03bdaa291481dd7e00e77a148aa0302267d47"
+                "sha256:2469240f6190aaebcb453033519eae69cfe8cc602065b4667e18ee14fc1e35dc",
+                "sha256:4fbace9a763285b608c06f01a807b51acb35f6059da6a01236654e08b0ee81ff"
             ],
             "index": "pypi",
-            "version": "==1.5.8"
+            "version": "==1.9.10"
         },
         "service-identity": {
             "hashes": [
@@ -803,6 +826,14 @@
             ],
             "version": "==21.1.0"
         },
+        "setuptools": {
+            "hashes": [
+                "sha256:512e5536220e38146176efb833d4a62aa726b7bbff82cfbc8ba9eaa3996e0b17",
+                "sha256:f62ea9da9ed6289bfe868cd6845968a2c854d1427f8548d52cae02a42b4f0356"
+            ],
+            "markers": "python_version >= '3.7'",
+            "version": "==65.5.0"
+        },
         "six": {
             "hashes": [
                 "sha256:1e61c37477a1626458e36f7b1d82aa5c9b094fa4802892072e49de9c60c4c926",
@@ -813,62 +844,62 @@
         },
         "sniffio": {
             "hashes": [
-                "sha256:471b71698eac1c2112a40ce2752bb2f4a4814c22a54a3eed3676bc0f5ca9f663",
-                "sha256:c4666eecec1d3f50960c6bdf61ab7bc350648da6c126e3cf6898d8cd4ddcd3de"
+                "sha256:e60305c5e5d314f5389259b7f22aaa33d8f7dee49763119234af3755c55b9101",
+                "sha256:eecefdce1e5bbfb7ad2eeaabf7c1eeb404d7757c379bd1f7e5cce9d8bf425384"
             ],
-            "markers": "python_version >= '3.5'",
-            "version": "==1.2.0"
+            "markers": "python_version >= '3.7'",
+            "version": "==1.3.0"
         },
         "soupsieve": {
             "hashes": [
-                "sha256:1a3cca2617c6b38c0343ed661b1fa5de5637f257d4fe22bd9f1338010a1efefb",
-                "sha256:b8d49b1cd4f037c7082a9683dfa1801aa2597fb11c3a1155b7a5b94829b4f1f9"
+                "sha256:3b2503d3c7084a42b1ebd08116e5f81aadfaea95863628c80a3b774a11b7c759",
+                "sha256:fc53893b3da2c33de295667a0e19f078c14bf86544af307354de5fcf12a3f30d"
             ],
-            "markers": "python_full_version >= '3.6.0'",
-            "version": "==2.3.1"
+            "markers": "python_version >= '3.6'",
+            "version": "==2.3.2.post1"
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         "sqlparse": {
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-            "version": "==0.4.2"
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         "twilio": {
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+            "version": "==7.14.2"
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             "extras": [
                 "tls"
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-            "version": "==22.2.0"
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+            "markers": "python_version >= '3.6'",
             "version": "==22.2.1"
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@@ -880,43 +911,57 @@
         },
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-            "version": "==1.26.9"
+            "markers": "python_version >= '3.6'",
+            "version": "==1.26.12"
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-            "version": "==0.17.6"
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@@ -930,15 +975,31 @@
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@@ -949,247 +1010,254 @@
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@@ -1257,27 +1334,27 @@
         },
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@@ -1288,11 +1365,11 @@
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@@ -1303,100 +1380,110 @@
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-                "sha256:ab5d89cfaf71807da93c131bb7a19c3e19eaefd613d14f3bce4e97de830b15df",
-                "sha256:b4829db3737480a9d5bfb1c0320c4ee13736f555f53a056aacc874f140e98f64",
-                "sha256:b52771f05cff7517f7067fef19ffe545b1f05959e440d42247a17cd9bddae11b",
-                "sha256:b8248f19a878c72d8c0a785a2cd45d69432e443c9f10ab924c29adda77b324ae",
-                "sha256:b9809404528a999cf02a400ee5677c81959bc5cb938fdc696b62eb40214e3632",
-                "sha256:c155a1a80c5e7a8fa1d9bb1bf3c8a953532b53ab1196092749bafb9d3a7cbb60",
-                "sha256:c33ce0c665dd325200209340a88438ba7a470bd5f09f7424e520e1a3ff835b52",
-                "sha256:c5adc854764732dbd95a713f2e6c3e914e17f2ccdc331b9ecb777484c31f73b6",
-                "sha256:cb374a2a4dba7c4be0b19dc7b1adc50e6c2c26c3369ac629f50f3c198f3743a4",
-                "sha256:cd00859291658fe1fda48a99559fb34da891c50385b0bfb35b808f98956ef1e7",
-                "sha256:ce3057777a14a9a1399b81eca6a6bfc9612047811234398b84c54aeff6d536ea",
-                "sha256:d0a5a1fdc9f148a8827d55b05425801acebeeefc9e86065c7ac8b8cc740a91ff",
-                "sha256:dad3991f0678facca1a0831ec1ddece2eb4d1dd0f5150acb9440f73a3b863907",
-                "sha256:dc7b7c16a519d924c50876fb152af661a20749dcbf653c8759e715c1a7a95b18",
-                "sha256:dcbb7665a9db9f8d7642171152c45da60e16c4f706191d66a1dc47ec9f820aed",
-                "sha256:df037c01d68d1958dad3463e2881d3638a0d6693483f58ad41001aa53a83fcea",
-                "sha256:f08a7e4d62ea2a45557f561eea87c907222575ca2134180b6974f8ac81e24f06",
-                "sha256:f16cf7e4e1bf88fecf7f41da4061f181a6170e179d956420f84e700fb8a3fd6b",
-                "sha256:f2c53f3af011393ab5ed9ab640fa0876757498aac188f782a0c620e33faa2a3d",
-                "sha256:f320c070dea3f20c11213e56dbbd7294c05743417cde01392148964b7bc2d31a",
-                "sha256:f553a1190ae6cd26e553a79f6b6cfba7b8f304da2071052fa33469da075ea625",
-                "sha256:fc8c7958d14e8270171b3d72792b609c057ec0fa17d507729835b5cff6b7f69a"
+                "sha256:4579f67d887f804e67edb544428f264b7b24f435b263c4614f384135cea553d2",
+                "sha256:491feb020dca48ccc562a8c0cbe8df07ee13078df59813b83959cbdada312ea3"
             ],
-            "markers": "python_version >= '3.6'",
-            "version": "==2022.3.15"
+            "markers": "python_full_version >= '3.6.0'",
+            "version": "==2.5.0"
         },
         "requests": {
             "hashes": [
-                "sha256:68d7c56fd5a8999887728ef304a6d12edc7be74f1cfa47714fc8b414525c9a61",
-                "sha256:f22fa1e554c9ddfd16e6e41ac79759e17be9e492b3587efa038054674760e72d"
+                "sha256:7c5599b102feddaa661c826c56ab4fee28bfd17f5abca1ebbe3e7f19d7c97983",
+                "sha256:8fefa2a1a1365bf5520aac41836fbee479da67864514bdb821f31ce07ce65349"
             ],
-            "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3, 3.4, 3.5'",
-            "version": "==2.27.1"
+            "markers": "python_version >= '3.7' and python_full_version < '4.0.0'",
+            "version": "==2.28.1"
         },
         "sqlparse": {
             "hashes": [
-                "sha256:0c00730c74263a94e5a9919ade150dfc3b19c574389985446148402998287dae",
-                "sha256:48719e356bb8b42991bdbb1e8b83223757b93789c00910a616a071910ca4a64d"
+                "sha256:0323c0ec29cd52bceabc1b4d9d579e311f3e4961b98d174201d5622a23b85e34",
+                "sha256:69ca804846bb114d2ec380e4360a8a340db83f0ccf3afceeb1404df028f57268"
             ],
             "markers": "python_version >= '3.5'",
-            "version": "==0.4.2"
+            "version": "==0.4.3"
         },
         "tblib": {
             "hashes": [
@@ -1540,58 +1549,21 @@
             "index": "pypi",
             "version": "==1.7.0"
         },
-        "testfixtures": {
-            "hashes": [
-                "sha256:02dae883f567f5b70fd3ad3c9eefb95912e78ac90be6c7444b5e2f46bf572c84",
-                "sha256:7de200e24f50a4a5d6da7019fb1197aaf5abd475efb2ec2422fdcf2f2eb98c1d"
-            ],
-            "version": "==6.18.5"
-        },
-        "toml": {
-            "hashes": [
-                "sha256:806143ae5bfb6a3c6e736a764057db0e6a0e05e338b5630894a5f779cabb4f9b",
-                "sha256:b3bda1d108d5dd99f4a20d24d9c348e91c4db7ab1b749200bded2f839ccbe68f"
-            ],
-            "markers": "python_version >= '2.6' and python_version not in '3.0, 3.1, 3.2, 3.3'",
-            "version": "==0.10.2"
-        },
-        "typed-ast": {
-            "hashes": [
-                "sha256:0eb77764ea470f14fcbb89d51bc6bbf5e7623446ac4ed06cbd9ca9495b62e36e",
-                "sha256:1098df9a0592dd4c8c0ccfc2e98931278a6c6c53cb3a3e2cf7e9ee3b06153344",
-                "sha256:183b183b7771a508395d2cbffd6db67d6ad52958a5fdc99f450d954003900266",
-                "sha256:18fe320f354d6f9ad3147859b6e16649a0781425268c4dde596093177660e71a",
-                "sha256:26a432dc219c6b6f38be20a958cbe1abffcc5492821d7e27f08606ef99e0dffd",
-                "sha256:294a6903a4d087db805a7656989f613371915fc45c8cc0ddc5c5a0a8ad9bea4d",
-                "sha256:31d8c6b2df19a777bc8826770b872a45a1f30cfefcfd729491baa5237faae837",
-                "sha256:33b4a19ddc9fc551ebabca9765d54d04600c4a50eda13893dadf67ed81d9a098",
-                "sha256:42c47c3b43fe3a39ddf8de1d40dbbfca60ac8530a36c9b198ea5b9efac75c09e",
-                "sha256:525a2d4088e70a9f75b08b3f87a51acc9cde640e19cc523c7e41aa355564ae27",
-                "sha256:58ae097a325e9bb7a684572d20eb3e1809802c5c9ec7108e85da1eb6c1a3331b",
-                "sha256:676d051b1da67a852c0447621fdd11c4e104827417bf216092ec3e286f7da596",
-                "sha256:74cac86cc586db8dfda0ce65d8bcd2bf17b58668dfcc3652762f3ef0e6677e76",
-                "sha256:8c08d6625bb258179b6e512f55ad20f9dfef019bbfbe3095247401e053a3ea30",
-                "sha256:90904d889ab8e81a956f2c0935a523cc4e077c7847a836abee832f868d5c26a4",
-                "sha256:963a0ccc9a4188524e6e6d39b12c9ca24cc2d45a71cfdd04a26d883c922b4b78",
-                "sha256:bbebc31bf11762b63bf61aaae232becb41c5bf6b3461b80a4df7e791fabb3aca",
-                "sha256:bc2542e83ac8399752bc16e0b35e038bdb659ba237f4222616b4e83fb9654985",
-                "sha256:c29dd9a3a9d259c9fa19d19738d021632d673f6ed9b35a739f48e5f807f264fb",
-                "sha256:c7407cfcad702f0b6c0e0f3e7ab876cd1d2c13b14ce770e412c0c4b9728a0f88",
-                "sha256:da0a98d458010bf4fe535f2d1e367a2e2060e105978873c04c04212fb20543f7",
-                "sha256:df05aa5b241e2e8045f5f4367a9f6187b09c4cdf8578bb219861c4e27c443db5",
-                "sha256:f290617f74a610849bd8f5514e34ae3d09eafd521dceaa6cf68b3f4414266d4e",
-                "sha256:f30ddd110634c2d7534b2d4e0e22967e88366b0d356b24de87419cc4410c41b7"
+        "tomli": {
+            "hashes": [
+                "sha256:939de3e7a6161af0c887ef91b7d41a53e7c5a1ca976325f429cb46ea9bc30ecc",
+                "sha256:de526c12914f0c550d15924c62d72abc48d6fe7364aa87328337a31007fe8a4f"
             ],
-            "markers": "python_version >= '3.6'",
-            "version": "==1.5.2"
+            "markers": "python_version < '3.11'",
+            "version": "==2.0.1"
         },
         "typing-extensions": {
             "hashes": [
-                "sha256:1a9462dcc3347a79b1f1c0271fbe79e844580bb598bafa1ed208b94da3cdcd42",
-                "sha256:21c85e0fe4b9a155d0799430b0ad741cdce7e359660ccbd8b530613e8df88ce2"
+                "sha256:1511434bb92bf8dd198c12b1cc812e800d4181cfcb867674e0f8279cc93087aa",
+                "sha256:16fa4864408f655d35ec496218b85f79b3437c829e93320c7c9215ccfd92489e"
             ],
             "index": "pypi",
-            "version": "==4.1.1"
+            "version": "==4.4.0"
         },
         "unittest-xml-reporting": {
             "hashes": [
@@ -1603,19 +1575,11 @@
         },
         "urllib3": {
             "hashes": [
-                "sha256:44ece4d53fb1706f667c9bd1c648f5469a2ec925fcf3a776667042d645472c14",
-                "sha256:aabaf16477806a5e1dd19aa41f8c2b7950dd3c746362d7e3223dbe6de6ac448e"
-            ],
-            "markers": "python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3, 3.4' and python_version < '4'",
-            "version": "==1.26.9"
-        },
-        "zipp": {
-            "hashes": [
-                "sha256:9f50f446828eb9d45b267433fd3e9da8d801f614129124863f9c51ebceafb87d",
-                "sha256:b47250dd24f92b7dd6a0a8fc5244da14608f3ca90a5efcd37a3b1642fac9a375"
+                "sha256:3fa96cf423e6987997fc326ae8df396db2a8b7c667747d47ddd8ecba91f4a74e",
+                "sha256:b930dd878d5a8afb066a637fbb35144fe7901e3b209d1cd4f524bd0e9deee997"
             ],
-            "markers": "python_version >= '3.7'",
-            "version": "==3.7.0"
+            "markers": "python_version >= '3.6'",
+            "version": "==1.26.12"
         }
     }
-}
\ No newline at end of file
+}
diff --git a/backend/officehoursqueue/settings/base.py b/backend/officehoursqueue/settings/base.py
index 682960fb8..fef717aad 100644
--- a/backend/officehoursqueue/settings/base.py
+++ b/backend/officehoursqueue/settings/base.py
@@ -14,6 +14,9 @@
 
 import dj_database_url
 
+from dotenv import load_dotenv
+
+load_dotenv()
 
 DOMAINS = os.environ.get("DOMAINS", "example.com").split(",")
 
@@ -185,3 +188,10 @@
 # Default to in-memory Channel Layer for dev and CI.
 
 CHANNEL_LAYERS = {"default": {"BACKEND": "channels.layers.InMemoryChannelLayer"}}
+
+
+# Upload file storage
+DEFAULT_FILE_STORAGE = "storages.backends.s3boto3.S3Boto3Storage"
+AWS_ACCESS_KEY_ID = os.environ.get('AWS_ACCESS_KEY_ID', None)
+AWS_SECRET_ACCESS_KEY = os.environ.get('AWS_SECRET_ACCESS_KEY', None)
+AWS_STORAGE_BUCKET_NAME = "ohq.question_files"
\ No newline at end of file
diff --git a/backend/ohq/admin.py b/backend/ohq/admin.py
index ac8c5d607..0ac1074c7 100644
--- a/backend/ohq/admin.py
+++ b/backend/ohq/admin.py
@@ -8,6 +8,7 @@
     MembershipInvite,
     Profile,
     Question,
+    QuestionFile,
     Queue,
     QueueStatistic,
     Semester,
@@ -15,14 +16,24 @@
 )
 
 
-admin.site.register(Course)
-admin.site.register(CourseStatistic)
-admin.site.register(Membership)
-admin.site.register(MembershipInvite)
-admin.site.register(Profile)
-admin.site.register(Question)
-admin.site.register(Queue)
-admin.site.register(Semester)
-admin.site.register(QueueStatistic)
-admin.site.register(Announcement)
-admin.site.register(Tag)
+class DisplayIdAdmin(admin.ModelAdmin):
+    readonly_fields = ("id",)
+
+    def get_list_display(self, request):
+        list_display = list(super().get_list_display(request))
+        list_display.insert(0, "id")
+        return list_display
+
+
+admin.site.register(Course, DisplayIdAdmin)
+admin.site.register(CourseStatistic, DisplayIdAdmin)
+admin.site.register(Membership, DisplayIdAdmin)
+admin.site.register(MembershipInvite, DisplayIdAdmin)
+admin.site.register(Profile, DisplayIdAdmin)
+admin.site.register(Question, DisplayIdAdmin)
+admin.site.register(Queue, DisplayIdAdmin)
+admin.site.register(Semester, DisplayIdAdmin)
+admin.site.register(QueueStatistic, DisplayIdAdmin)
+admin.site.register(Announcement, DisplayIdAdmin)
+admin.site.register(Tag, DisplayIdAdmin)
+admin.site.register(QuestionFile, DisplayIdAdmin)
diff --git a/backend/ohq/forms.py b/backend/ohq/forms.py
new file mode 100644
index 000000000..995a5bdef
--- /dev/null
+++ b/backend/ohq/forms.py
@@ -0,0 +1,5 @@
+from django import forms
+
+
+class UploadFileForm(forms.Form):
+    file = forms.FileField(widget=forms.ClearableFileInput(attrs={"multiple": True}))
diff --git a/backend/ohq/management/commands/createcourse.py b/backend/ohq/management/commands/createcourse.py
index dc6bc4053..fd51966d8 100644
--- a/backend/ohq/management/commands/createcourse.py
+++ b/backend/ohq/management/commands/createcourse.py
@@ -17,7 +17,9 @@ def add_arguments(self, parser):
         parser.add_argument("year", type=int)
         parser.add_argument("--emails", nargs="+", type=str)
         parser.add_argument(
-            "--roles", nargs="+", choices=[Membership.KIND_PROFESSOR, Membership.KIND_HEAD_TA],
+            "--roles",
+            nargs="+",
+            choices=[Membership.KIND_PROFESSOR, Membership.KIND_HEAD_TA],
         )
 
     def handle(self, *args, **kwargs):
diff --git a/backend/ohq/migrations/0002_auto_20200816_1727.py b/backend/ohq/migrations/0002_auto_20200816_1727.py
index 08eff3815..57a9f3ff1 100644
--- a/backend/ohq/migrations/0002_auto_20200816_1727.py
+++ b/backend/ohq/migrations/0002_auto_20200816_1727.py
@@ -14,15 +14,38 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.RenameField(
-            model_name="question", old_name="time_answered", new_name="time_responded_to",
+            model_name="question",
+            old_name="time_answered",
+            new_name="time_responded_to",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="answered_by",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="rejected_by",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="rejected_reason_other",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="time_last_updated",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="time_rejected",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="time_started",
+        ),
+        migrations.RemoveField(
+            model_name="question",
+            name="time_withdrawn",
         ),
-        migrations.RemoveField(model_name="question", name="answered_by",),
-        migrations.RemoveField(model_name="question", name="rejected_by",),
-        migrations.RemoveField(model_name="question", name="rejected_reason_other",),
-        migrations.RemoveField(model_name="question", name="time_last_updated",),
-        migrations.RemoveField(model_name="question", name="time_rejected",),
-        migrations.RemoveField(model_name="question", name="time_started",),
-        migrations.RemoveField(model_name="question", name="time_withdrawn",),
         migrations.AddField(
             model_name="question",
             name="responded_to_by",
diff --git a/backend/ohq/migrations/0004_auto_20200825_1344.py b/backend/ohq/migrations/0004_auto_20200825_1344.py
index 9c074b708..6b891339b 100644
--- a/backend/ohq/migrations/0004_auto_20200825_1344.py
+++ b/backend/ohq/migrations/0004_auto_20200825_1344.py
@@ -11,6 +11,8 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.AlterField(
-            model_name="queue", name="estimated_wait_time", field=models.IntegerField(default=-1),
+            model_name="queue",
+            name="estimated_wait_time",
+            field=models.IntegerField(default=-1),
         ),
     ]
diff --git a/backend/ohq/migrations/0005_auto_20201016_1702.py b/backend/ohq/migrations/0005_auto_20201016_1702.py
index 4820ad327..7f639d64c 100644
--- a/backend/ohq/migrations/0005_auto_20201016_1702.py
+++ b/backend/ohq/migrations/0005_auto_20201016_1702.py
@@ -16,6 +16,8 @@ class Migration(migrations.Migration):
             field=models.CharField(blank=True, max_length=255, null=True),
         ),
         migrations.AddField(
-            model_name="question", name="resolved_note", field=models.BooleanField(default=True),
+            model_name="question",
+            name="resolved_note",
+            field=models.BooleanField(default=True),
         ),
     ]
diff --git a/backend/ohq/migrations/0008_auto_20210119_2218.py b/backend/ohq/migrations/0008_auto_20210119_2218.py
index abd48cd8d..365d866a1 100644
--- a/backend/ohq/migrations/0008_auto_20210119_2218.py
+++ b/backend/ohq/migrations/0008_auto_20210119_2218.py
@@ -11,7 +11,9 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.AddField(
-            model_name="queue", name="rate_limit_enabled", field=models.BooleanField(default=False),
+            model_name="queue",
+            name="rate_limit_enabled",
+            field=models.BooleanField(default=False),
         ),
         migrations.AddField(
             model_name="queue",
diff --git a/backend/ohq/migrations/0010_auto_20210407_0145.py b/backend/ohq/migrations/0010_auto_20210407_0145.py
index 7669354f3..f37c6ea01 100644
--- a/backend/ohq/migrations/0010_auto_20210407_0145.py
+++ b/backend/ohq/migrations/0010_auto_20210407_0145.py
@@ -10,5 +10,9 @@ class Migration(migrations.Migration):
     ]
 
     operations = [
-        migrations.AlterField(model_name="announcement", name="content", field=models.TextField(),),
+        migrations.AlterField(
+            model_name="announcement",
+            name="content",
+            field=models.TextField(),
+        ),
     ]
diff --git a/backend/ohq/migrations/0013_auto_20210924_2056.py b/backend/ohq/migrations/0013_auto_20210924_2056.py
index cd3f50451..b67e7cae3 100644
--- a/backend/ohq/migrations/0013_auto_20210924_2056.py
+++ b/backend/ohq/migrations/0013_auto_20210924_2056.py
@@ -10,6 +10,12 @@ class Migration(migrations.Migration):
     ]
 
     operations = [
-        migrations.RemoveField(model_name="course", name="require_video_chat_url_on_questions",),
-        migrations.RemoveField(model_name="course", name="video_chat_enabled",),
+        migrations.RemoveField(
+            model_name="course",
+            name="require_video_chat_url_on_questions",
+        ),
+        migrations.RemoveField(
+            model_name="course",
+            name="video_chat_enabled",
+        ),
     ]
diff --git a/backend/ohq/migrations/0016_auto_20211008_2136.py b/backend/ohq/migrations/0016_auto_20211008_2136.py
index dbd187d41..4b49534ae 100644
--- a/backend/ohq/migrations/0016_auto_20211008_2136.py
+++ b/backend/ohq/migrations/0016_auto_20211008_2136.py
@@ -11,7 +11,9 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.AddField(
-            model_name="queue", name="pin_enabled", field=models.BooleanField(default=False),
+            model_name="queue",
+            name="pin_enabled",
+            field=models.BooleanField(default=False),
         ),
         migrations.AddField(
             model_name="queue",
diff --git a/backend/ohq/migrations/0018_auto_20220125_0344.py b/backend/ohq/migrations/0018_auto_20220125_0344.py
index 374deeaff..967cdbd37 100644
--- a/backend/ohq/migrations/0018_auto_20220125_0344.py
+++ b/backend/ohq/migrations/0018_auto_20220125_0344.py
@@ -11,6 +11,8 @@ class Migration(migrations.Migration):
 
     operations = [
         migrations.AlterField(
-            model_name="course", name="course_title", field=models.CharField(max_length=100),
+            model_name="course",
+            name="course_title",
+            field=models.CharField(max_length=100),
         ),
     ]
diff --git a/backend/ohq/migrations/0020_questionfile.py b/backend/ohq/migrations/0020_questionfile.py
new file mode 100644
index 000000000..9c43f6bd9
--- /dev/null
+++ b/backend/ohq/migrations/0020_questionfile.py
@@ -0,0 +1,32 @@
+# Generated by Django 3.1.7 on 2022-04-17 17:53
+
+import django.db.models.deletion
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ("ohq", "0019_auto_20211114_1800"),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name="QuestionFile",
+            fields=[
+                (
+                    "id",
+                    models.AutoField(
+                        auto_created=True, primary_key=True, serialize=False, verbose_name="ID"
+                    ),
+                ),
+                ("file", models.FileField(upload_to="question_files/")),
+                (
+                    "question",
+                    models.ForeignKey(
+                        on_delete=django.db.models.deletion.CASCADE, to="ohq.question"
+                    ),
+                ),
+            ],
+        ),
+    ]
diff --git a/backend/ohq/models.py b/backend/ohq/models.py
index a3284c0a8..ab946d9ad 100644
--- a/backend/ohq/models.py
+++ b/backend/ohq/models.py
@@ -1,3 +1,5 @@
+import os
+
 from django.conf import settings
 from django.core.validators import MaxValueValidator, MinValueValidator
 from django.db import models
@@ -411,3 +413,20 @@ class Announcement(models.Model):
     author = models.ForeignKey(User, related_name="announcements", on_delete=models.CASCADE)
     time_updated = models.DateTimeField(auto_now=True)
     course = models.ForeignKey(Course, related_name="announcements", on_delete=models.CASCADE)
+
+
+class QuestionFile(models.Model):
+    question = models.ForeignKey(Question, on_delete=models.CASCADE)
+    file = models.FileField(upload_to="question_files/")
+
+
+# Delete file on delete of QuestionFile object
+@receiver(models.signals.post_delete, sender=QuestionFile)
+def auto_delete_file_on_delete(sender, instance, **kwargs):
+    """
+    Deletes file from filesystem
+    when corresponding `QuestionFile` object is deleted.
+    """
+    if instance.file:
+        if os.path.isfile(instance.file.path):
+            os.remove(instance.file.path)
diff --git a/backend/ohq/permissions.py b/backend/ohq/permissions.py
index eb026abaf..29a16f247 100644
--- a/backend/ohq/permissions.py
+++ b/backend/ohq/permissions.py
@@ -2,7 +2,7 @@
 from rest_framework import permissions
 from schedule.models import Event, EventRelation, Occurrence
 
-from ohq.models import Course, Membership, Question
+from ohq.models import Course, Membership, Question, QuestionFile
 
 
 # Hierarchy of permissions is usually:
@@ -130,12 +130,30 @@ class QuestionPermission(permissions.BasePermission):
 
     def has_object_permission(self, request, view, obj):
         membership = Membership.objects.get(course=view.kwargs["course_pk"], user=request.user)
-
         # Students can get or modify their own question
         # TAs+ can get or modify any questions
-        if view.action in ["retrieve", "update", "partial_update", "position"]:
+        if view.action in [
+            "retrieve",
+            "update",
+            "partial_update",
+            "position",
+            "upload_file",
+            "delete_all_file",
+        ]:
             return obj.asked_by == request.user or membership.is_ta
 
+        if view.action in ["delete_file"]:
+            if not (obj.asked_by == request.user or membership.is_ta):
+                return False
+
+            # all file ids must correspond
+            attempted_ids = request.GET.getlist("ids")
+            available_ids = QuestionFile.objects.filter(question=obj).values_list("id", flat=True)
+            for attempt in attempted_ids:
+                if attempt not in available_ids:
+                    return False
+            return True
+
     def has_permission(self, request, view):
         # Anonymous users can't do anything
         if not request.user.is_authenticated:
@@ -167,6 +185,10 @@ def has_permission(self, request, view):
 
             return membership.kind == Membership.KIND_STUDENT and existing_question is None
 
+        if view.action in ["upload_file", "delete_file", "delete_all_file"]:
+            question = Question.objects.get(pk=view.kwargs["pk"])
+            return self.has_object_permission(request, view, question)
+
         # Students+ can get, list, or modify questions
         # With restrictions defined in has_object_permission
         return True
diff --git a/backend/ohq/schemas.py b/backend/ohq/schemas.py
index 63a282e0d..984d8dde3 100644
--- a/backend/ohq/schemas.py
+++ b/backend/ohq/schemas.py
@@ -38,6 +38,36 @@ def get_operation(self, path, method):
         return operation
 
 
+class QuestionSchema(AutoSchema):
+    def get_operation(self, path, method):
+        op = super().get_operation(path, method)
+        if op["operationId"] == "uploadFileQuestion":
+            op["requestBody"] = {
+                "content": {
+                    "multipart/form-data": {
+                        "schema": {
+                            "properties": {
+                                "file": {"type": "array of files"},
+                            }
+                        }
+                    }
+                }
+            }
+        elif op["operationId"] == "deleteFileQuestion":
+            op["parameters"].append(
+                {
+                    "name": "id",
+                    "in": "query",
+                    "required": False,
+                    "description": "A series of ids of files to be deleted <br>"
+                    + "e.g. /deleteFile/?id=1&id=2 "
+                    + "- where the numbers are the file pks",
+                    "schema": {"type": "string"},
+                }
+            )
+        return op
+
+
 class EventSchema(AutoSchema):
     def get_operation(self, path, method):
         op = super().get_operation(path, method)
@@ -47,7 +77,7 @@ def get_operation(self, path, method):
                     "name": "course",
                     "in": "query",
                     "required": True,
-                    "description": "A series of api/events/?course=1&course=2 "
+                    "description": "A series of /events/?course=1&course=2 "
                     + "- where the numbers are the course pks",
                     "schema": {"type": "string"},
                 }
@@ -64,7 +94,7 @@ def get_operation(self, path, method):
                     "name": "course",
                     "in": "query",
                     "required": True,
-                    "description": "A series of api/occurrences/?course=1&course=2 "
+                    "description": "A series of occurrences/?course=1&course=2 "
                     + "- where the numbers are the course pks",
                     "schema": {"type": "string"},
                 }
diff --git a/backend/ohq/serializers.py b/backend/ohq/serializers.py
index 0b704ed0f..487af651d 100644
--- a/backend/ohq/serializers.py
+++ b/backend/ohq/serializers.py
@@ -18,6 +18,7 @@
     MembershipInvite,
     Profile,
     Question,
+    QuestionFile,
     Queue,
     QueueStatistic,
     Semester,
@@ -214,6 +215,7 @@ class QuestionSerializer(QueueRouteMixin):
     responded_to_by = UserSerializer(read_only=True)
     tags = TagSerializer(many=True)
     position = serializers.IntegerField(default=-1, read_only=True)
+    files = serializers.ListField(child=serializers.CharField(), read_only=True, required=False)
 
     class Meta:
         model = Question
@@ -234,6 +236,7 @@ class Meta:
             "resolved_note",
             "position",
             "student_descriptor",
+            "files",
         )
         read_only_fields = (
             "time_asked",
@@ -244,6 +247,7 @@ class Meta:
             "should_send_up_soon_notification",
             "resolved_note",
             "position",
+            "files",
         )
 
     def update(self, instance, validated_data):
@@ -254,7 +258,6 @@ def update(self, instance, validated_data):
         user = self.context["request"].user
         membership = Membership.objects.get(course=instance.queue.course, user=user)
         queue_id = self.context["view"].kwargs["queue_pk"]
-
         if membership.is_ta:  # User is a TA+
             if "status" in validated_data:
                 status = validated_data["status"]
@@ -343,6 +346,15 @@ def create(self, validated_data):
                 continue
         return question
 
+    def to_representation(self, instance):
+        representation = super().to_representation(instance)
+        question_files = QuestionFile.objects.filter(question=instance).all()
+        question_file_ids = []
+        for question_file in question_files:
+            question_file_ids.append(question_file.id)
+        representation["files"] = question_file_ids
+        return representation
+
 
 class MembershipPrivateSerializer(CourseRouteMixin):
     """
diff --git a/backend/ohq/statistics.py b/backend/ohq/statistics.py
index 93bf31e62..b65260681 100644
--- a/backend/ohq/statistics.py
+++ b/backend/ohq/statistics.py
@@ -120,7 +120,9 @@ def course_calculate_instructor_most_time_helping(course, last_sunday):
 
 def queue_calculate_avg_wait(queue, date):
     avg = Question.objects.filter(
-        queue=queue, time_asked__date=date, time_response_started__isnull=False,
+        queue=queue,
+        time_asked__date=date,
+        time_response_started__isnull=False,
     ).aggregate(avg_wait=Avg(F("time_response_started") - F("time_asked")))
 
     wait = avg["avg_wait"]
@@ -172,7 +174,9 @@ def queue_calculate_wait_time_heatmap(queue, weekday, hour):
 
 def queue_calculate_num_questions_ans(queue, date):
     num_questions = Question.objects.filter(
-        queue=queue, status=Question.STATUS_ANSWERED, time_responded_to__date=date,
+        queue=queue,
+        status=Question.STATUS_ANSWERED,
+        time_responded_to__date=date,
     ).count()
 
     QueueStatistic.objects.update_or_create(
@@ -186,7 +190,9 @@ def queue_calculate_num_questions_ans(queue, date):
 def queue_calculate_num_students_helped(queue, date):
     num_students = (
         Question.objects.filter(
-            queue=queue, status=Question.STATUS_ANSWERED, time_responded_to__date=date,
+            queue=queue,
+            status=Question.STATUS_ANSWERED,
+            time_responded_to__date=date,
         )
         .distinct("asked_by")
         .count()
@@ -206,7 +212,8 @@ def queue_calculate_questions_per_ta_heatmap(queue, weekday, hour):
         .annotate(date=TruncDate("time_asked"))
         .values("date")
         .annotate(
-            questions=Count("date", distinct=False), tas=Count("responded_to_by", distinct=True),
+            questions=Count("date", distinct=False),
+            tas=Count("responded_to_by", distinct=True),
         )
         .annotate(
             q_per_ta=Case(When(tas=0, then=F("questions")), default=1.0 * F("questions") / F("tas"))
diff --git a/backend/ohq/views.py b/backend/ohq/views.py
index 3dbfc2720..d49d5fed3 100644
--- a/backend/ohq/views.py
+++ b/backend/ohq/views.py
@@ -33,6 +33,7 @@
 from schedule.models import Event, EventRelationManager, Occurrence
 
 from ohq.filters import CourseStatisticFilter, QuestionSearchFilter, QueueStatisticFilter
+from ohq.forms import UploadFileForm
 from ohq.invite import parse_and_send_invites
 from ohq.models import (
     Announcement,
@@ -41,6 +42,7 @@
     Membership,
     MembershipInvite,
     Question,
+    QuestionFile,
     Queue,
     QueueStatistic,
     Semester,
@@ -63,7 +65,7 @@
     QueueStatisticPermission,
     TagPermission,
 )
-from ohq.schemas import EventSchema, MassInviteSchema, OccurrenceSchema
+from ohq.schemas import EventSchema, MassInviteSchema, OccurrenceSchema, QuestionSchema
 from ohq.serializers import (
     AnnouncementSerializer,
     CourseCreateSerializer,
@@ -205,6 +207,8 @@ class QuestionViewSet(viewsets.ModelViewSet, RealtimeMixin):
     permission_classes = [QuestionPermission | IsSuperuser]
     serializer_class = QuestionSerializer
     queryset = Question.objects.none()
+    form_class = UploadFileForm
+    schema = QuestionSchema()
 
     def get_queryset(self):
         position = (
@@ -225,7 +229,11 @@ def get_queryset(self):
             )
             .annotate(
                 position=Case(
-                    When(status=Question.STATUS_ASKED, then=Subquery(position[:1]),), default=-1,
+                    When(
+                        status=Question.STATUS_ASKED,
+                        then=Subquery(position[:1]),
+                    ),
+                    default=-1,
                 )
             )
             .order_by("time_asked")
@@ -342,6 +350,57 @@ def quota_count(self, request, course_pk, queue_pk):
         else:
             return JsonResponse({"detail": "queue does not have rate limit"}, status=405)
 
+    def handle_file_upload(self, uploaded_file, question):
+        question_file = QuestionFile(question=question, file=uploaded_file)
+        question_file.save()
+        return question_file
+
+    @action(detail=True, methods=["post"])
+    def upload_file(self, request, *args, **kwargs):
+        if request.method == "POST":
+            form = self.form_class(request.POST, request.FILES)
+            if form.is_valid():
+                question = Question.objects.filter(pk=self.kwargs["pk"]).first()
+                response = []
+
+                # projecting up total storage
+                current_storage = 0
+                current_qfiles = QuestionFile.objects.filter(question=question).all()
+                for qfile in current_qfiles:
+                    current_storage += qfile.file.size
+                for file in request.FILES.getlist("file"):
+                    current_storage += file.size
+                if current_storage > 5 * 1024 * 1024:  # if total storage exceeds 5MB
+                    return JsonResponse(
+                        {
+                            "detail": "files are too heavy. "
+                            + "total storage for this question exceed 5MB"
+                        },
+                        status=413,
+                    )
+
+                # creating files in storage
+                for file in request.FILES.getlist("file"):
+                    question_file = self.handle_file_upload(file, question)
+                    response.append({"id": question_file.id, "name": question_file.file.name})
+                return JsonResponse(response, status=200, safe=False)
+            else:
+                return JsonResponse({"detail": form.errors.as_text}, status=406)
+        return JsonResponse({"detail": "file upload should be POST"}, status=405)
+
+    @action(detail=True, methods=["delete"])
+    def delete_file(self, request, *args, **kwargs):
+        question_file_ids = request.GET.getlist("id")
+        QuestionFile.objects.filter(pk__in=question_file_ids).delete()
+        return JsonResponse({"detail": "Success"}, status=200)
+
+    @action(detail=True, methods=["delete"])
+    def delete_all_file(self, request, *args, **kwargs):
+        question = Question.objects.filter(pk=self.kwargs["pk"]).first()
+        question_files = QuestionFile.objects.filter(question=question)
+        question_files.delete()
+        return JsonResponse({"detail": "Success"}, status=200)
+
 
 class QuestionSearchView(XLSXFileMixin, generics.ListAPIView):
     filter_backends = [DjangoFilterBackend]
@@ -425,7 +484,9 @@ def get_queryset(self):
             )
             .order_by()
             .values("course")
-            .annotate(count=Count("*", output_field=FloatField()),)
+            .annotate(
+                count=Count("*", output_field=FloatField()),
+            )
             .values("count")
         )
 
diff --git a/backend/tests/ohq/test_live.py b/backend/tests/ohq/test_live.py
index 22ed9b31c..9dd4671fa 100644
--- a/backend/tests/ohq/test_live.py
+++ b/backend/tests/ohq/test_live.py
@@ -38,7 +38,9 @@ async def asyncSetUp(self):
             course=self.course, user=self.student2, kind=Membership.KIND_STUDENT
         )
         self.old_question = await db(Question.objects.create)(
-            queue=self.queue, asked_by=self.student1, text="Help me",
+            queue=self.queue,
+            asked_by=self.student1,
+            text="Help me",
         )
 
         headers = await get_headers_for_user(self.student2)
diff --git a/backend/tests/ohq/test_models.py b/backend/tests/ohq/test_models.py
index 360210ff2..3e1141a66 100644
--- a/backend/tests/ohq/test_models.py
+++ b/backend/tests/ohq/test_models.py
@@ -198,7 +198,8 @@ def test_metric_to_pretty(self):
         )
 
         self.assertEqual(
-            self.student_time_being_helped.metric_to_pretty(), "Student: Time being helped",
+            self.student_time_being_helped.metric_to_pretty(),
+            "Student: Time being helped",
         )
 
         self.assertEqual(
diff --git a/backend/tests/ohq/test_permissions.py b/backend/tests/ohq/test_permissions.py
index 9d4667c60..1941ec7c2 100644
--- a/backend/tests/ohq/test_permissions.py
+++ b/backend/tests/ohq/test_permissions.py
@@ -3,6 +3,7 @@
 
 import pytz
 from django.contrib.auth import get_user_model
+from django.core.files.uploadedfile import SimpleUploadedFile
 from django.test import TestCase
 from django.urls import reverse
 from parameterized import parameterized
@@ -15,6 +16,7 @@
     Membership,
     MembershipInvite,
     Question,
+    QuestionFile,
     Queue,
     Semester,
     Tag,
@@ -713,8 +715,47 @@ def setUp(self):
     @parameterized.expand(users, name_func=get_test_name)
     def test_list(self, user):
         test(
-            self, user, "list", "get", reverse("ohq:questionsearch", args=[self.course.id]),
+            self,
+            user,
+            "list",
+            "get",
+            reverse("ohq:questionsearch", args=[self.course.id]),
+        )
+
+
+class QuestionFileTestCase(TestCase):
+    def setUp(self):
+        setUp(self)
+        self.queue = Queue.objects.create(name="Queue", course=self.course)
+        self.question = Question.objects.create(queue=self.queue, asked_by=self.student)
+        self.question_other = Question.objects.create(queue=self.queue, asked_by=self.ta)
+        file = SimpleUploadedFile("file.txt", b"file_content")
+        self.question_file = QuestionFile(question=self.question, file=file)
+        self.question_file.save()
+        # Expected results
+        self.expected = {
+            "delete-file": {
+                "ta": 200,
+                "student": 403,
+            },
+        }
+
+    @parameterized.expand(["student", "ta"], name_func=get_test_name)
+    def test_delete_files(self, user):
+        # the question is asked by TA, so student can't delete
+        test(
+            self,
+            user,
+            "delete-file",
+            "delete",
+            reverse(
+                "ohq:question-delete-file",
+                args=[self.course.id, self.queue.id, self.question_other.id],
+            )
+            + "?id="
+            + str(self.question_file.id),
         )
+        QuestionFile.objects.all().delete()
 
 
 class MembershipTestCase(TestCase):
@@ -977,7 +1018,11 @@ def setUp(self):
     @parameterized.expand(users, name_func=get_test_name)
     def test_list(self, user):
         test(
-            self, user, "list", "get", reverse("ohq:course-statistic", args=[self.course.id]),
+            self,
+            user,
+            "list",
+            "get",
+            reverse("ohq:course-statistic", args=[self.course.id]),
         )
 
 
@@ -1196,7 +1241,11 @@ def test_create(self, user):
     @parameterized.expand(users, name_func=get_test_name)
     def test_retrieve(self, user):
         test(
-            self, user, "retrieve", "get", reverse("ohq:event-detail", args=[self.event.id]),
+            self,
+            user,
+            "retrieve",
+            "get",
+            reverse("ohq:event-detail", args=[self.event.id]),
         )
 
     @parameterized.expand(users, name_func=get_test_name)
diff --git a/backend/tests/ohq/test_queues.py b/backend/tests/ohq/test_queues.py
index 663da4614..e9f1ca6bd 100644
--- a/backend/tests/ohq/test_queues.py
+++ b/backend/tests/ohq/test_queues.py
@@ -31,22 +31,34 @@ def setUp(self):
 
         self.now = timezone.now()
         q1 = Question.objects.create(
-            queue=self.open_queue, asked_by=self.student, text="Q1", time_response_started=self.now,
+            queue=self.open_queue,
+            asked_by=self.student,
+            text="Q1",
+            time_response_started=self.now,
         )
         q1.time_asked = self.now - timedelta(minutes=3)
         q1.save()
         q2 = Question.objects.create(
-            queue=self.open_queue, asked_by=self.student, text="Q2", time_response_started=self.now,
+            queue=self.open_queue,
+            asked_by=self.student,
+            text="Q2",
+            time_response_started=self.now,
         )
         q2.time_asked = self.now - timedelta(minutes=3)
         q2.save()
         q3 = Question.objects.create(
-            queue=self.open_queue, asked_by=self.student, text="Q3", time_response_started=self.now,
+            queue=self.open_queue,
+            asked_by=self.student,
+            text="Q3",
+            time_response_started=self.now,
         )
         q3.time_asked = self.now - timedelta(minutes=4)
         q3.save()
         q4 = Question.objects.create(
-            queue=self.open_queue, asked_by=self.student, text="Q4", time_response_started=self.now,
+            queue=self.open_queue,
+            asked_by=self.student,
+            text="Q4",
+            time_response_started=self.now,
         )
         q4.time_asked = self.now - timedelta(minutes=6)
         q4.save()
diff --git a/backend/tests/ohq/test_serializers.py b/backend/tests/ohq/test_serializers.py
index 2010c641f..f70f354d8 100644
--- a/backend/tests/ohq/test_serializers.py
+++ b/backend/tests/ohq/test_serializers.py
@@ -53,7 +53,8 @@ def test_verify_phone_number_invalid(self):
         self.serializer.update(self.user, {"profile": {"phone_number": "+15555555555"}})
         with self.assertRaises(serializers.ValidationError):
             self.serializer.update(
-                self.user, {"profile": {"sms_verification_code": "ABC123"}},
+                self.user,
+                {"profile": {"sms_verification_code": "ABC123"}},
             )
 
     def test_verify_phone_number_time_expired(self):
diff --git a/backend/tests/ohq/test_views.py b/backend/tests/ohq/test_views.py
index 06a4a3b5a..d62433003 100644
--- a/backend/tests/ohq/test_views.py
+++ b/backend/tests/ohq/test_views.py
@@ -2,6 +2,7 @@
 from datetime import timedelta
 
 from django.contrib.auth import get_user_model
+from django.core.files.uploadedfile import SimpleUploadedFile
 from django.test import TestCase
 from django.urls import reverse
 from django.utils import timezone
@@ -9,7 +10,7 @@
 from rest_framework.test import APIClient
 from schedule.models import Event, Occurrence
 
-from ohq.models import Course, Membership, MembershipInvite, Question, Queue, Semester
+from ohq.models import Course, Membership, MembershipInvite, Question, QuestionFile, Queue, Semester
 from ohq.serializers import UserPrivateSerializer
 
 
@@ -138,7 +139,9 @@ def setUp(self):
         )
         self.no_limit_queue = Queue.objects.create(name="No Rate Limit Queue", course=self.course)
         self.ta = User.objects.create(username="ta")
-        self.student = User.objects.create(username="student")
+        self.student = User.objects.create(
+            username="student"
+        )  # note student is rate-limited on test_rate_limit
         self.student2 = User.objects.create(username="student2")
         self.student3 = User.objects.create(username="student3")
         Membership.objects.create(course=self.course, user=self.ta, kind=Membership.KIND_TA)
@@ -192,23 +195,32 @@ def setUp(self):
         self.prelimit_question1.time_responded_to = timezone.now() - timedelta(minutes=6)
         self.prelimit_question.save()
         self.prelimit_question1.save()
-
         Question.objects.create(queue=self.queue3, asked_by=self.student3, text="Help me")
 
+        self.question_with_file = Question.objects.create(
+            queue=self.queue, asked_by=self.student3, text="Help me with the files"
+        )
+        self.file1 = SimpleUploadedFile("file.txt", b"file_content")
+        self.file2 = SimpleUploadedFile("file2.txt", b"file_content 2")
+        self.question_file1 = QuestionFile(question=self.question_with_file, file=self.file1)
+        self.question_file2 = QuestionFile(question=self.question_with_file, file=self.file2)
+        self.question_file1.save()
+        self.question_file2.save()
+
     def test_rate_limit(self):
         self.client.force_authenticate(user=self.student)
         self.client.patch(
             reverse("ohq:question-detail", args=[self.course.id, self.queue.id, self.question.id]),
             {"status": Question.STATUS_ANSWERED},
         )
-        self.assertEqual(7, Question.objects.all().count())
+        self.assertEqual(8, Question.objects.all().count())
 
         res = self.client.post(
             reverse("ohq:question-list", args=[self.course.id, self.queue.id]),
             {"text": "Should be rate limited", "tags": []},
         )
         self.assertEqual(429, res.status_code)
-        self.assertEqual(7, Question.objects.all().count())
+        self.assertEqual(8, Question.objects.all().count())
 
         res = self.client.get(
             reverse("ohq:question-quota-count", args=[self.course.id, self.queue.id])
@@ -225,7 +237,7 @@ def test_rate_limit(self):
             reverse("ohq:question-list", args=[self.course.id, self.queue.id]),
             {"text": "Shouldn't be rate limited", "tags": []},
         )
-        self.assertEqual(8, Question.objects.all().count())
+        self.assertEqual(9, Question.objects.all().count())
 
         self.client.force_authenticate(user=self.student3)
         res = self.client.get(
@@ -268,6 +280,80 @@ def test_create_with_pin(self):
         )
         self.assertEqual(2, Question.objects.all().count())
 
+    def test_upload_file(self):
+        self.client.force_authenticate(user=self.student)
+        # uploading single file
+        QuestionFile.objects.all().delete()
+
+        file = SimpleUploadedFile("file.txt", b"file_content")
+        response = self.client.post(
+            reverse(
+                "ohq:question-upload-file", args=[self.course.id, self.queue.id, self.question.id]
+            ),
+            {"file": [file]},
+            format="multipart",
+        )
+        response_data = json.loads(response.content)
+        self.assertEquals(1, len(response_data))
+        self.assertEquals(1, QuestionFile.objects.all().count())
+
+        # uploading multiple files
+        QuestionFile.objects.all().delete()
+        self.assertEquals(0, QuestionFile.objects.all().count())
+        file = SimpleUploadedFile("file1.txt", b"file content")
+        file2 = SimpleUploadedFile("file2.txt", b"file_content")
+        response = self.client.post(
+            reverse(
+                "ohq:question-upload-file", args=[self.course.id, self.queue.id, self.question.id]
+            ),
+            {"file": [file, file2]},
+            format="multipart",
+        )
+        response_data = json.loads(response.content)
+        self.assertEquals(2, QuestionFile.objects.all().count())
+        self.assertEquals(2, len(response_data))
+
+        # getting file list in response
+        response = self.client.get(
+            reverse("ohq:question-detail", args=[self.course.id, self.queue.id, self.question.id])
+        )
+        response_data = json.loads(response.content)
+        self.assertEqual(2, len(response_data["files"]))
+        QuestionFile.objects.all().delete()
+
+    def test_delete_file(self):
+        self.client.force_authenticate(user=self.student3)
+        file1_pk = str(self.question_file1.pk)
+        self.client.delete(
+            reverse(
+                "ohq:question-delete-file",
+                args=[self.course.id, self.queue.id, self.question_with_file.id],
+            )
+            + "?id="
+            + file1_pk
+        )
+        self.assertEqual(1, QuestionFile.objects.all().count())
+
+        # doing again won't delete more
+        self.client.delete(
+            reverse(
+                "ohq:question-delete-file",
+                args=[self.course.id, self.queue.id, self.question_with_file.id],
+            )
+            + "?id="
+            + file1_pk
+        )
+        self.assertEqual(1, QuestionFile.objects.all().count())
+
+        # deleting all files
+        self.client.delete(
+            reverse(
+                "ohq:question-delete-all-file",
+                args=[self.course.id, self.queue.id, self.question_with_file.id],
+            )
+        )
+        self.assertEqual(0, QuestionFile.objects.all().count())
+
 
 class OccurrenceViewTestCase(TestCase):
     def setUp(self):
@@ -307,7 +393,8 @@ def test_list(self):
             },
         )
         response = self.client.get(
-            "/api/occurrences/?course="
+            reverse("ohq:occurrence-list")
+            + "?course="
             + str(self.course.id)
             + "&filter_start="
             + self.filter_start