diff --git a/backend/windmill-api/openapi.yaml b/backend/windmill-api/openapi.yaml
index 0700504ab0..ee1a974346 100644
--- a/backend/windmill-api/openapi.yaml
+++ b/backend/windmill-api/openapi.yaml
@@ -22988,10 +22988,9 @@ components:
         - flow
         - job
     AssetUsageAccessType:
-      oneOf:
-        - type: string
-          enum: [r, w, rw]
-        - type: 'null'
+      type: string
+      enum: [r, w, rw]
+      nullable: true
     AssetKind:
       type: string
       enum:
diff --git a/cli/windmill-utils-internal/src/path-utils/path-assigner.ts b/cli/windmill-utils-internal/src/path-utils/path-assigner.ts
index 4b67e06abf..3fedbd8d37 100644
--- a/cli/windmill-utils-internal/src/path-utils/path-assigner.ts
+++ b/cli/windmill-utils-internal/src/path-utils/path-assigner.ts
@@ -34,6 +34,7 @@ export const LANGUAGE_EXTENSIONS: Record<SupportedLanguage, string> = {
   java: "java",
   duckdb: "duckdb.sql",
   bunnative: "ts",
+  ruby: "rb",
   // for related places search: ADD_NEW_LANG
 };
 
@@ -82,6 +83,7 @@ export const EXTENSION_TO_LANGUAGE: Record<string, SupportedLanguage> = {
   "playbook.yml": "ansible",
   "java": "java",
   "duckdb.sql": "duckdb",
+  "rb": "ruby",
   // Plain .ts defaults to bun (will be overridden by defaultTs setting)
   "ts": "bun",
 };
diff --git a/frontend/src/lib/components/assets/lib.ts b/frontend/src/lib/components/assets/lib.ts
index c991ecc46b..2dacedbae3 100644
--- a/frontend/src/lib/components/assets/lib.ts
+++ b/frontend/src/lib/components/assets/lib.ts
@@ -9,9 +9,9 @@ import type {
 import { capitalize } from '$lib/utils'
 export type Asset = _Asset
 export type AssetKind = _AssetKind
-export type AssetWithAccessType = Asset & { access_type?: AssetUsageAccessType }
+export type AssetWithAccessType = Asset & { access_type?: AssetUsageAccessType | null }
 export type AssetWithAltAccessType = AssetWithAccessType & {
-	alt_access_type?: AssetUsageAccessType
+	alt_access_type?: AssetUsageAccessType | null
 	columns?: Record<string, AssetUsageAccessType>
 }
 export type AssetUsage = ListAssetsResponse['assets'][number]['usages'][number]
diff --git a/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts b/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
index 2e0d05ee0f..8ba95e0dac 100644
--- a/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
+++ b/frontend/src/lib/components/copilot/chat/AIChatManager.svelte.ts
@@ -538,6 +538,7 @@ class AIChatManager {
 			console.log('chatRequest error', err)
 			console.error('chatRequest error', err)
 			callbacks.onMessageEnd()
+			this.cancelLoadingTools()
 			if (!abortController.signal.aborted) {
 				throw err
 			}
@@ -835,18 +836,7 @@ class AIChatManager {
 			abortController: this.abortController
 		})
 		this.abortController?.abort(cancelReason)
-		// Mark all tool messages in loading state as canceled
-		this.displayMessages = this.displayMessages.map((message) => {
-			if (message.role === 'tool' && message.isLoading) {
-				return {
-					...message,
-					isLoading: false,
-					content: 'Canceled',
-					error: 'Canceled'
-				}
-			}
-			return message
-		})
+		this.cancelLoadingTools()
 	}
 
 	cancelInlineRequest = (reason?: string) => {
@@ -1202,6 +1192,20 @@ class AIChatManager {
 			this.cachedDatatables = []
 		}
 	}
+
+	cancelLoadingTools = () => {
+		this.displayMessages = this.displayMessages.map((message) => {
+			if (message.role === 'tool' && message.isLoading) {
+				return {
+					...message,
+					isLoading: false,
+					content: 'Canceled',
+					error: 'Canceled'
+				}
+			}
+			return message
+		})
+	}
 }
 
 export const aiChatManager = new AIChatManager()
diff --git a/openflow.openapi.yaml b/openflow.openapi.yaml
index 1c0346db2d..feb67b413c 100644
--- a/openflow.openapi.yaml
+++ b/openflow.openapi.yaml
@@ -653,13 +653,15 @@ components:
                   - ducklake
                   - datatable
               access_type:
-                type: [string, "null"]
+                type: string
+                nullable: true
                 description: Access level for this asset
-                enum: [r, w, rw, null]
+                enum: [r, w, rw]
               alt_access_type:
-                type: [string, "null"]
+                type: string
+                nullable: true
                 description: Alternative access level
-                enum: [r, w, rw, null]
+                enum: [r, w, rw]
       required:
         - type
         - content