diff --git a/apps/desktop/src/utils/tag-generation.ts b/apps/desktop/src/utils/tag-generation.ts
index 4d136f6342..ed02b93cf0 100644
--- a/apps/desktop/src/utils/tag-generation.ts
+++ b/apps/desktop/src/utils/tag-generation.ts
@@ -6,63 +6,68 @@ import { commands as templateCommands } from "@hypr/plugin-template";
 import { generateText, localProviderName, modelProvider } from "@hypr/utils/ai";
 
 export async function generateTagsForSession(sessionId: string): Promise<string[]> {
-  const { type: connectionType } = await connectorCommands.getLlmConnection();
+  try {
+    const { type: connectionType } = await connectorCommands.getLlmConnection();
 
-  const config = await dbCommands.getConfig();
-  const session = await dbCommands.getSession({ id: sessionId });
-  if (!session) {
-    throw new Error("Session not found");
-  }
+    const config = await dbCommands.getConfig();
+    const session = await dbCommands.getSession({ id: sessionId });
+    if (!session) {
+      throw new Error("Session not found");
+    }
 
-  const historicalTags = await dbCommands.listAllTags();
-  const currentTags = await dbCommands.listSessionTags(sessionId);
+    const historicalTags = await dbCommands.listAllTags();
+    const currentTags = await dbCommands.listSessionTags(sessionId);
 
-  const extractHashtags = (text: string): string[] => {
-    const hashtagRegex = /#(\w+)/g;
-    return Array.from(text.matchAll(hashtagRegex), match => match[1]);
-  };
+    const extractHashtags = (text: string): string[] => {
+      const hashtagRegex = /#(\w+)/g;
+      return Array.from(text.matchAll(hashtagRegex), match => match[1]);
+    };
 
-  const existingHashtags = extractHashtags(session.raw_memo_html);
+    const existingHashtags = extractHashtags(session.raw_memo_html);
 
-  const systemPrompt = await templateCommands.render(
-    "suggest_tags.system",
-    { config, type: connectionType },
-  );
+    const systemPrompt = await templateCommands.render(
+      "suggest_tags.system",
+      { config, type: connectionType },
+    );
 
-  const userPrompt = await templateCommands.render(
-    "suggest_tags.user",
-    {
-      title: session.title,
-      content: session.raw_memo_html,
-      existing_hashtags: existingHashtags,
-      formal_tags: currentTags.map(t => t.name),
-      historical_tags: historicalTags.slice(0, 20).map(t => t.name),
-    },
-  );
+    const userPrompt = await templateCommands.render(
+      "suggest_tags.user",
+      {
+        title: session.title,
+        content: session.raw_memo_html,
+        existing_hashtags: existingHashtags,
+        formal_tags: currentTags.map(t => t.name),
+        historical_tags: historicalTags.slice(0, 20).map(t => t.name),
+      },
+    );
 
-  const provider = await modelProvider();
-  const model = provider.languageModel("defaultModel");
+    const provider = await modelProvider();
+    const model = provider.languageModel("defaultModel");
 
-  const result = await generateText({
-    model,
-    messages: [
-      { role: "system", content: systemPrompt },
-      { role: "user", content: userPrompt },
-    ],
-    providerOptions: {
-      [localProviderName]: {
-        metadata: {
-          grammar: "tags",
+    const result = await generateText({
+      model,
+      messages: [
+        { role: "system", content: systemPrompt },
+        { role: "user", content: userPrompt },
+      ],
+      providerOptions: {
+        [localProviderName]: {
+          metadata: {
+            grammar: "tags",
+          },
         },
       },
-    },
-  });
+    });
 
-  const schema = z.preprocess(
-    (val) => (typeof val === "string" ? JSON.parse(val) : val),
-    z.array(z.string().min(1)).min(1).max(5),
-  );
+    const schema = z.preprocess(
+      (val) => (typeof val === "string" ? JSON.parse(val) : val),
+      z.array(z.string().min(1)).min(1).max(5),
+    );
 
-  const parsed = schema.safeParse(result.text);
-  return parsed.success ? parsed.data : [];
+    const parsed = schema.safeParse(result.text);
+    return parsed.success ? parsed.data : [];
+  } catch (error) {
+    console.error("Tag generation failed:", error);
+    return [];
+  }
 }
diff --git a/crates/gbnf/assets/tags.gbnf b/crates/gbnf/assets/tags.gbnf
index 6638c24bdb..b17423cc1c 100644
--- a/crates/gbnf/assets/tags.gbnf
+++ b/crates/gbnf/assets/tags.gbnf
@@ -1,3 +1,3 @@
-root ::= "[" "'" word "'" ("," ws "'" word "'")* "]"
+root ::= "[" "\"" word "\"" ("," ws "\"" word "\"")* "]"
 word ::= [a-zA-Z0-9_-]+
 ws ::= " "*
\ No newline at end of file
diff --git a/crates/gbnf/src/lib.rs b/crates/gbnf/src/lib.rs
index d93e80ceb7..a9f8a3c622 100644
--- a/crates/gbnf/src/lib.rs
+++ b/crates/gbnf/src/lib.rs
@@ -47,8 +47,8 @@ mod tests {
         let gbnf = gbnf_validator::Validator::new().unwrap();
 
         for (input, expected) in vec![
-            ("['meeting', 'summary']", true),
-            ("['meeting', 'summary', '']", false),
+            ("[\"meeting\", \"summary\"]", true),
+            ("[\"meeting\", \"summary\", \"\"]", false),
         ] {
             let result = gbnf.validate(TAGS, input).unwrap();
             assert_eq!(result, expected, "failed: {}", input);