diff --git a/test_cases/test_in_condition_float_context_comma_delimited_floats__should_match.jsonc b/test_cases/test_in_condition_float_context_comma_delimited_floats__should_match.jsonc
new file mode 100644
index 0000000..962b07a
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_comma_delimited_floats__should_match.jsonc
@@ -0,0 +1,45 @@
+{
+  // Given: A segment with IN condition using comma-delimited floats
+  // When: An evaluation context with an identity that has a float trait matching one of the comma-delimited float values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_comma_delim_user",
+      "key": "key_float_comma_delim_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "34": {
+        "key": "34",
+        "name": "segment_float_comma_delimited",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": "1.0,2.0,3.0,4.0"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_float_comma_delimited"
+      }
+    ]
+  }
+}
diff --git a/test_cases/test_in_condition_float_context_comma_delimited_ints__should_not_match.jsonc b/test_cases/test_in_condition_float_context_comma_delimited_ints__should_not_match.jsonc
new file mode 100644
index 0000000..f9719e4
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_comma_delimited_ints__should_not_match.jsonc
@@ -0,0 +1,41 @@
+{
+  // Given: A segment with IN condition using comma-delimited integers
+  // When: An evaluation context with an identity that has a float trait that does not match any of the comma-delimited integer values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_comma_delim_int_user",
+      "key": "key_float_comma_delim_int_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "36": {
+        "key": "36",
+        "name": "segment_float_comma_delimited_int_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": "1,2,3,4"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_float_context_float_array__should_match.jsonc b/test_cases/test_in_condition_float_context_float_array__should_match.jsonc
new file mode 100644
index 0000000..37ce54a
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_float_array__should_match.jsonc
@@ -0,0 +1,50 @@
+{
+  // Given: A segment with IN condition using an array of floats
+  // When: An evaluation context with an identity that has a float trait matching one of the array values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_array_user",
+      "key": "key_float_array_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "30": {
+        "key": "30",
+        "name": "segment_float_array",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": [
+                  "1.0",
+                  "2.0",
+                  "3.0",
+                  "4.0"
+                ]
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_float_array"
+      }
+    ]
+  }
+}
diff --git a/test_cases/test_in_condition_float_context_int_array__should_not_match.jsonc b/test_cases/test_in_condition_float_context_int_array__should_not_match.jsonc
new file mode 100644
index 0000000..3233edf
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_int_array__should_not_match.jsonc
@@ -0,0 +1,46 @@
+{
+  // Given: A segment with IN condition using an array of integers
+  // When: An evaluation context with an identity that has a float trait that does not match any of the integer array values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_int_array_user",
+      "key": "key_float_int_array_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "32": {
+        "key": "32",
+        "name": "segment_float_int_array_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": [
+                  "1",
+                  "2",
+                  "3",
+                  "4"
+                ]
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_float_context_json_encoded_floats__should_match.jsonc b/test_cases/test_in_condition_float_context_json_encoded_floats__should_match.jsonc
new file mode 100644
index 0000000..60e395b
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_json_encoded_floats__should_match.jsonc
@@ -0,0 +1,45 @@
+{
+  // Given: A segment with IN condition using JSON-encoded array of floats
+  // When: An evaluation context with an identity that has a float trait matching one of the JSON-encoded float values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_json_array_user",
+      "key": "key_float_json_array_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "38": {
+        "key": "38",
+        "name": "segment_float_json_encoded",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": "[1.0,2.0,3.0,4.0]"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_float_json_encoded"
+      }
+    ]
+  }
+}
diff --git a/test_cases/test_in_condition_float_context_json_encoded_ints__should_not_match.jsonc b/test_cases/test_in_condition_float_context_json_encoded_ints__should_not_match.jsonc
new file mode 100644
index 0000000..1afd68e
--- /dev/null
+++ b/test_cases/test_in_condition_float_context_json_encoded_ints__should_not_match.jsonc
@@ -0,0 +1,41 @@
+{
+  // Given: A segment with IN condition using JSON-encoded array of integers
+  // When: An evaluation context with an identity that has a float trait that does not match any of the JSON-encoded integer values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "float_json_int_array_user",
+      "key": "key_float_json_int_array_user",
+      "traits": {
+        "score": 2.0
+      }
+    },
+    "segments": {
+      "40": {
+        "key": "40",
+        "name": "segment_float_json_encoded_int_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "score",
+                "value": "[1,2,3,4]"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_comma_delimited_floats__should_not_match.jsonc b/test_cases/test_in_condition_int_context_comma_delimited_floats__should_not_match.jsonc
new file mode 100644
index 0000000..5074878
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_comma_delimited_floats__should_not_match.jsonc
@@ -0,0 +1,41 @@
+{
+  // Given: A segment with IN condition using comma-delimited floats
+  // When: An evaluation context with an identity that has an integer trait that does not match any of the comma-delimited float values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_comma_delim_float_user",
+      "key": "key_int_comma_delim_float_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "37": {
+        "key": "37",
+        "name": "segment_int_comma_delimited_float_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": "1.0,2.0,3.0,4.0"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_comma_delimited_ints__should_match.jsonc b/test_cases/test_in_condition_int_context_comma_delimited_ints__should_match.jsonc
new file mode 100644
index 0000000..87ed357
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_comma_delimited_ints__should_match.jsonc
@@ -0,0 +1,45 @@
+{
+  // Given: A segment with IN condition using comma-delimited integers
+  // When: An evaluation context with an identity that has an integer trait matching one of the comma-delimited integer values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_comma_delim_user",
+      "key": "key_int_comma_delim_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "35": {
+        "key": "35",
+        "name": "segment_int_comma_delimited",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": "1,2,3,4"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_int_comma_delimited"
+      }
+    ]
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_float_array__should_not_match.jsonc b/test_cases/test_in_condition_int_context_float_array__should_not_match.jsonc
new file mode 100644
index 0000000..427853a
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_float_array__should_not_match.jsonc
@@ -0,0 +1,46 @@
+{
+  // Given: A segment with IN condition using an array of floats
+  // When: An evaluation context with an identity that has an integer trait that does not match any of the float array values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_float_array_user",
+      "key": "key_int_float_array_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "33": {
+        "key": "33",
+        "name": "segment_int_float_array_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": [
+                  "1.0",
+                  "2.0",
+                  "3.0",
+                  "4.0"
+                ]
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_int_array__should_match.jsonc b/test_cases/test_in_condition_int_context_int_array__should_match.jsonc
new file mode 100644
index 0000000..cf582c1
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_int_array__should_match.jsonc
@@ -0,0 +1,50 @@
+{
+  // Given: A segment with IN condition using an array of integers
+  // When: An evaluation context with an identity that has an integer trait matching one of the array values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_array_user",
+      "key": "key_int_array_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "31": {
+        "key": "31",
+        "name": "segment_int_array",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": [
+                  "1",
+                  "2",
+                  "3",
+                  "4"
+                ]
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_int_array"
+      }
+    ]
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_json_encoded_floats__should_not_match.jsonc b/test_cases/test_in_condition_int_context_json_encoded_floats__should_not_match.jsonc
new file mode 100644
index 0000000..f900c6b
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_json_encoded_floats__should_not_match.jsonc
@@ -0,0 +1,41 @@
+{
+  // Given: A segment with IN condition using JSON-encoded array of floats
+  // When: An evaluation context with an identity that has an integer trait that does not match any of the JSON-encoded float values
+  // Then: The context should not be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_json_float_array_user",
+      "key": "key_int_json_float_array_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "41": {
+        "key": "41",
+        "name": "segment_int_json_encoded_float_mismatch",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": "[1.0,2.0,3.0,4.0]"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": []
+  }
+}
diff --git a/test_cases/test_in_condition_int_context_json_encoded_ints__should_match.jsonc b/test_cases/test_in_condition_int_context_json_encoded_ints__should_match.jsonc
new file mode 100644
index 0000000..b02d3e0
--- /dev/null
+++ b/test_cases/test_in_condition_int_context_json_encoded_ints__should_match.jsonc
@@ -0,0 +1,45 @@
+{
+  // Given: A segment with IN condition using JSON-encoded array of integers
+  // When: An evaluation context with an identity that has an integer trait matching one of the JSON-encoded integer values
+  // Then: The context should be considered part of the segment
+  "$schema": "https://raw.githubusercontent.com/Flagsmith/engine-test-data/refs/tags/v2.0.0/schema.json",
+  "context": {
+    "environment": {
+      "key": "key",
+      "name": "Environment"
+    },
+    "identity": {
+      "identifier": "int_json_array_user",
+      "key": "key_int_json_array_user",
+      "traits": {
+        "level": 2
+      }
+    },
+    "segments": {
+      "39": {
+        "key": "39",
+        "name": "segment_int_json_encoded",
+        "rules": [
+          {
+            "type": "ALL",
+            "conditions": [
+              {
+                "operator": "IN",
+                "property": "level",
+                "value": "[1,2,3,4]"
+              }
+            ]
+          }
+        ]
+      }
+    }
+  },
+  "result": {
+    "flags": {},
+    "segments": [
+      {
+        "name": "segment_int_json_encoded"
+      }
+    ]
+  }
+}