diff --git a/packages/compass-collection/src/components/collection-header-actions/collection-header-actions.tsx b/packages/compass-collection/src/components/collection-header-actions/collection-header-actions.tsx
index 772724035f3..036ca238716 100644
--- a/packages/compass-collection/src/components/collection-header-actions/collection-header-actions.tsx
+++ b/packages/compass-collection/src/components/collection-header-actions/collection-header-actions.tsx
@@ -125,11 +125,17 @@ const CollectionHeaderActions: React.FunctionComponent<
     !hasSchemaAnalysisData &&
     schemaAnalysisStatus !== SCHEMA_ANALYSIS_STATE_ANALYZING;
 
+  const hasSchemaAnalysisUnsupportedStateError = Boolean(
+    schemaAnalysisError && schemaAnalysisError.errorType === 'unsupportedState'
+  );
+
   const isView = isReadonly && sourceName && !editViewName;
 
   const showViewEdit = isView && !preferencesReadWrite;
   const shouldDisableMockDataButton =
-    !hasSchemaAnalysisData || exceedsMaxNestingDepth;
+    !hasSchemaAnalysisData ||
+    exceedsMaxNestingDepth ||
+    hasSchemaAnalysisUnsupportedStateError;
 
   const onMockDataGeneratorCtaButtonClicked = useCallback(() => {
     track('Mock Data Generator Opened', {
@@ -184,7 +190,11 @@ const CollectionHeaderActions: React.FunctionComponent<
       )}
       {shouldShowMockDataButton && (
         <Tooltip
-          enabled={exceedsMaxNestingDepth || isCollectionEmpty}
+          enabled={
+            exceedsMaxNestingDepth ||
+            isCollectionEmpty ||
+            hasSchemaAnalysisUnsupportedStateError
+          }
           trigger={
             <div>
               <Button
@@ -199,29 +209,22 @@ const CollectionHeaderActions: React.FunctionComponent<
             </div>
           }
         >
-          {/* TODO(CLOUDP-333853): update disabled open-modal button
-          tooltip to communicate if schema analysis is incomplete */}
           <>
-            {exceedsMaxNestingDepth && (
+            {hasSchemaAnalysisUnsupportedStateError ? (
+              <span className={tooltipMessageStyles}>
+                {schemaAnalysisError?.errorMessage}
+              </span>
+            ) : exceedsMaxNestingDepth ? (
               <span className={tooltipMessageStyles}>
                 At this time we are unable to generate mock data for collections
                 that have deeply nested documents.
               </span>
-            )}
-            {isCollectionEmpty && (
+            ) : isCollectionEmpty ? (
               <span className={tooltipMessageStyles}>
                 Please add data to your collection to generate similar mock
                 documents.
               </span>
-            )}
-            {schemaAnalysisError &&
-              schemaAnalysisError.errorType === 'unsupportedState' && (
-                <span className={tooltipMessageStyles}>
-                  This collection has a field with a name that contains a
-                  &quot.&quot, which mock data generation does not support at
-                  this time.
-                </span>
-              )}
+            ) : null}
           </>
         </Tooltip>
       )}
diff --git a/packages/compass-collection/src/transform-schema-to-field-info.spec.ts b/packages/compass-collection/src/transform-schema-to-field-info.spec.ts
index c2b9d2f671b..a4eb7a86706 100644
--- a/packages/compass-collection/src/transform-schema-to-field-info.spec.ts
+++ b/packages/compass-collection/src/transform-schema-to-field-info.spec.ts
@@ -1344,7 +1344,120 @@ describe('processSchema', function () {
       };
 
       expect(() => processSchema(schema)).to.throw(
-        "invalid fieldPath '[]': field parts must have characters other than '[]'"
+        ProcessSchemaUnsupportedStateError,
+        "Feature is unsupported for field names that end with '[]'; field name: '[]'"
+      );
+    });
+
+    it('throws error for field names ending with []', function () {
+      const schema: Schema = {
+        fields: [
+          {
+            name: 'users[]',
+            path: ['users[]'],
+            count: 1,
+            type: ['String'],
+            probability: 1.0,
+            hasDuplicates: false,
+            types: [
+              {
+                name: 'String',
+                bsonType: 'String',
+                path: ['users[]'],
+                count: 1,
+                probability: 1.0,
+                values: ['test'],
+              },
+            ],
+          },
+        ],
+        count: 1,
+      };
+
+      expect(() => processSchema(schema)).to.throw(
+        ProcessSchemaUnsupportedStateError,
+        "Feature is unsupported for field names that end with '[]'; field name: 'users[]'"
+      );
+    });
+
+    it('throws error for nested field names ending with []', function () {
+      const schema: Schema = {
+        fields: [
+          {
+            name: 'parent',
+            path: ['parent'],
+            count: 1,
+            type: ['Document'],
+            probability: 1.0,
+            hasDuplicates: false,
+            types: [
+              {
+                name: 'Document',
+                bsonType: 'Document',
+                path: ['parent'],
+                count: 1,
+                probability: 1.0,
+                fields: [
+                  {
+                    name: 'child[]',
+                    path: ['parent', 'child[]'],
+                    count: 1,
+                    type: ['String'],
+                    probability: 1.0,
+                    hasDuplicates: false,
+                    types: [
+                      {
+                        name: 'String',
+                        bsonType: 'String',
+                        path: ['parent', 'child[]'],
+                        count: 1,
+                        probability: 1.0,
+                        values: ['test'],
+                      },
+                    ],
+                  },
+                ],
+              },
+            ],
+          },
+        ],
+        count: 1,
+      };
+
+      expect(() => processSchema(schema)).to.throw(
+        ProcessSchemaUnsupportedStateError,
+        "Feature is unsupported for field names that end with '[]'; field name: 'child[]'"
+      );
+    });
+
+    it('throws error for field names containing dots', function () {
+      const schema: Schema = {
+        fields: [
+          {
+            name: 'user.name',
+            path: ['user.name'],
+            count: 1,
+            type: ['String'],
+            probability: 1.0,
+            hasDuplicates: false,
+            types: [
+              {
+                name: 'String',
+                bsonType: 'String',
+                path: ['user.name'],
+                count: 1,
+                probability: 1.0,
+                values: ['test'],
+              },
+            ],
+          },
+        ],
+        count: 1,
+      };
+
+      expect(() => processSchema(schema)).to.throw(
+        ProcessSchemaUnsupportedStateError,
+        "Feature is unsupported for field names that contain a '.'; field name: 'user.name'"
       );
     });
   });
diff --git a/packages/compass-collection/src/transform-schema-to-field-info.ts b/packages/compass-collection/src/transform-schema-to-field-info.ts
index f87c8b7de1a..516a8fdc038 100644
--- a/packages/compass-collection/src/transform-schema-to-field-info.ts
+++ b/packages/compass-collection/src/transform-schema-to-field-info.ts
@@ -244,7 +244,13 @@ function processNamedField(
 
   if (field.name.includes(FIELD_NAME_SEPARATOR)) {
     throw new ProcessSchemaUnsupportedStateError(
-      `no support for field names that contain a '${FIELD_NAME_SEPARATOR}' ; field name: '${field.name}'`
+      `Feature is unsupported for field names that contain a '${FIELD_NAME_SEPARATOR}'; field name: '${field.name}'`
+    );
+  }
+
+  if (field.name.endsWith('[]')) {
+    throw new ProcessSchemaUnsupportedStateError(
+      `Feature is unsupported for field names that end with '[]'; field name: '${field.name}'`
     );
   }