diff --git a/openapi/components/codeSamples/files.yaml b/openapi/components/codeSamples/files.yaml
index 8ede989b..6b48f300 100644
--- a/openapi/components/codeSamples/files.yaml
+++ b/openapi/components/codeSamples/files.yaml
@@ -79,3 +79,25 @@
       source: >-
         curl -X GET "https://api.vrchat.cloud/api/1/analysis/{fileId}/{versionId}/standard" \
              -b "auth={authCookie}"
+/icon:
+  post:
+    - lang: cURL
+      source: >-
+        curl -X POST "https://api.vrchat.cloud/api/1/icon" \
+             -b "auth={authCookie}" \
+             -F "file=@/path/to/image.png"
+/gallery:
+  post:
+    - lang: cURL
+      source: >-
+        curl -X POST "https://api.vrchat.cloud/api/1/gallery" \
+             -b "auth={authCookie}" \
+             -F "file=@/path/to/image.png"
+/file/image:
+  post:
+    - lang: cURL
+      source: >-
+        curl -X POST "https://api.vrchat.cloud/api/1/file/image" \
+             -b "auth={authCookie}" \
+             -F "file=@/path/to/image.png" \ 
+             -F "tag=icon"
diff --git a/openapi/components/paths.yaml b/openapi/components/paths.yaml
index a8f39dba..4e55bffe 100644
--- a/openapi/components/paths.yaml
+++ b/openapi/components/paths.yaml
@@ -108,6 +108,12 @@
   $ref: "./paths/files.yaml#/paths/~1analysis~1{fileId}~1{versionId}~1security"
 "/analysis/{fileId}/{versionId}/standard":
   $ref: "./paths/files.yaml#/paths/~1analysis~1{fileId}~1{versionId}~1standard"
+"/file/image":
+  $ref: "./paths/files.yaml#/paths/~1file~1image"
+"/icon":
+  $ref: "./paths/files.yaml#/paths/~1icon"
+"/gallery":
+  $ref: "./paths/files.yaml#/paths/~1gallery"
 
 # friends
 
diff --git a/openapi/components/paths/files.yaml b/openapi/components/paths/files.yaml
index 3d5d46fd..b5c32c33 100644
--- a/openapi/components/paths/files.yaml
+++ b/openapi/components/paths/files.yaml
@@ -294,6 +294,96 @@ paths:
       security:
         - authCookie: []
       description: Get the standard performance analysis for the uploaded assets of an avatar
+  '/file/image':
+    post:
+      summary: Upload gallery image, icon, emoji or sticker
+      tags:
+        - files
+      x-codeSamples:
+        $ref: "../codeSamples/files.yaml#/~1file~1image/post"
+      responses:
+        '200':
+          $ref: ../responses/files/FileResponse.yaml
+      operationId: uploadImage
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+                  description: The binary blob of the png file.
+                tag:
+                  type: string
+                  description: Needs to be either icon, gallery, sticker or emoji
+                animationStyle:
+                  type: string
+                  example: bats
+                  description: Animation style for sticker, required for emoji.
+                maskTag:
+                  type: string
+                  example: square
+                  description: Mask of the sticker, optional for emoji.
+              required:
+                - file
+                - tag
+      security:
+        - authCookie: []
+      description: Upload an image, which can be an icon, gallery image, sticker or emoji
+  '/icon':
+    post:
+      summary: Upload icon
+      tags:
+        - files
+      x-codeSamples:
+        $ref: "../codeSamples/files.yaml#/~1icon/post"
+      responses:
+        '200':
+          $ref: ../responses/files/FileResponse.yaml
+      operationId: uploadIcon
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+                  description: The binary blob of the png file.
+              required:
+                - file
+      security:
+        - authCookie: [ ]
+      description: Upload an icon
+  '/gallery':
+    post:
+      summary: Upload gallery image
+      tags:
+        - files
+      x-codeSamples:
+        $ref: "../codeSamples/files.yaml#/~1gallery/post"
+      responses:
+        '200':
+          $ref: ../responses/files/FileResponse.yaml
+      operationId: uploadGalleryImage
+      requestBody:
+        content:
+          multipart/form-data:
+            schema:
+              type: object
+              properties:
+                file:
+                  type: string
+                  format: binary
+                  description: The binary blob of the png file.
+              required:
+                - file
+      security:
+        - authCookie: [ ]
+      description: Upload a gallery image
 tags:
   $ref: ../tags.yaml
 components:
diff --git a/openapi/components/schemas/File.yaml b/openapi/components/schemas/File.yaml
index 4701755f..fef2351e 100644
--- a/openapi/components/schemas/File.yaml
+++ b/openapi/components/schemas/File.yaml
@@ -1,5 +1,11 @@
 description: ''
 properties:
+  animationStyle:
+    type: string
+    example: bats
+  maskTag:
+    type: string
+    example: square
   extension:
     example: .unitypackage
     minLength: 1