diff --git a/Networking/Networking/Remote/MediaRemote.swift b/Networking/Networking/Remote/MediaRemote.swift
index d3ea16b803f..7fb630ae3c2 100644
--- a/Networking/Networking/Remote/MediaRemote.swift
+++ b/Networking/Networking/Remote/MediaRemote.swift
@@ -89,7 +89,7 @@ public class MediaRemote: Remote, MediaRemoteProtocol {
                                  completion: @escaping (Result<[Media], Error>) -> Void) {
         let parameters: [String: Any] = [
             ParameterKey.contextKey: context ?? Default.context,
-            ParameterKey.pageSize: pageSize,
+            ParameterKey.dotComPageSize: pageSize,
             ParameterKey.pageNumber: pageNumber,
             ParameterKey.fields: "ID,date,URL,thumbnails,title,alt,extension,mime_type,file",
             ParameterKey.mimeType: imagesOnly ? "image" : nil,
@@ -123,10 +123,10 @@ public class MediaRemote: Remote, MediaRemoteProtocol {
                                                   pageSize: Int = 25,
                                                   completion: @escaping (Result<[WordPressMedia], Error>) -> Void) {
         let parameters: [String: Any] = [
-            ParameterKey.pageSize: pageSize,
+            ParameterKey.dotOrgPageSize: pageSize,
             ParameterKey.pageNumber: pageNumber,
             ParameterKey.fieldsWordPressSite: ParameterValue.wordPressMediaFields,
-            ParameterKey.mimeType: imagesOnly ? "image" : nil,
+            ParameterKey.mediaType: imagesOnly ? "image" : nil,
             ParameterKey.wordPressMediaParent: productID
         ].compactMapValues { $0 }
 
@@ -294,13 +294,23 @@ public extension MediaRemote {
 
     private enum ParameterKey {
         static let pageNumber: String = "page"
-        static let pageSize: String   = "number"
+        // For dotcom API usage, we want to use "number"
+        // https://developer.wordpress.com/docs/api/1.2/get/sites/%24site/media/
+        static let dotComPageSize: String = "number"
+        // For dotorg API usage, we want to use "per_page"
+        // https://developer.wordpress.org/rest-api/reference/media/#arguments
+        static let dotOrgPageSize: String = "per_page"
         static let wordPressMediaPostID: String = "post"
         static let altText: String = "alt"
         static let wordPressAltText: String = "alt_text"
         static let fields: String     = "fields"
         static let fieldsWordPressSite: String = "_fields"
+        // For dotcom API usage, we want to use "mime_type"
+        // https://developer.wordpress.com/docs/api/1.2/get/sites/%24site/media/
         static let mimeType: String   = "mime_type"
+        // For dotorg API usage, we want to use "media_type"
+        // https://developer.wordpress.org/rest-api/reference/media/#list-media
+        static let mediaType: String = "media_type"
         static let postID: String   = "post_ID"
         static let contextKey: String = "context"
         static let wordPressMediaParentID = "parent_id"
diff --git a/RELEASE-NOTES.txt b/RELEASE-NOTES.txt
index 80f7c3f3e2f..cc39d25dc1b 100644
--- a/RELEASE-NOTES.txt
+++ b/RELEASE-NOTES.txt
@@ -13,6 +13,7 @@
 - [*] Menu tab > Payments: in the "deposits" summary view at the top, all mentions of "deposits/deposit/deposited" have been renamed to "payouts/payout/paid out" respectively to match the renaming in web. [https://github.com/woocommerce/woocommerce-ios/pull/14402]
 - [*] Receipts: Added message confirming receipt sent to customer after successful payment. [https://github.com/woocommerce/woocommerce-ios/pull/14390]
 - [internal] Simplifies App Icon by only using a single image for all supported platforms. [https://github.com/woocommerce/woocommerce-ios/pull/14429]
+- [**] Media Library: On sites logged in with application password, when picking image from WordPress Media Library, all images will now load correctly. [https://github.com/woocommerce/woocommerce-ios/pull/14444]
 - [*] Dashboard: Performance card now shows cached Visitors and Conversion data correctly. [https://github.com/woocommerce/woocommerce-ios/pull/14438]
 
 21.1