diff --git a/.changeset/smooth-rice-chew.md b/.changeset/smooth-rice-chew.md
new file mode 100644
index 0000000000..a845151cc8
--- /dev/null
+++ b/.changeset/smooth-rice-chew.md
@@ -0,0 +1,2 @@
+---
+---
diff --git a/server/src/addie/mcp/url-tools.ts b/server/src/addie/mcp/url-tools.ts
index 887e9ac787..fde6589409 100644
--- a/server/src/addie/mcp/url-tools.ts
+++ b/server/src/addie/mcp/url-tools.ts
@@ -118,8 +118,8 @@ export const URL_TOOLS: AddieTool[] = [
   {
     name: 'read_slack_file',
     description:
-      'Download and read a file that was shared in Slack. Use this when a user shares a file (PDF, document, text file, etc.) and asks about its contents. Provide the file URL from the shared file info.',
-    usage_hints: 'use when user shares a file in Slack and asks "what is in this file?", "can you read this?"',
+      'Download and read a file that was shared in Slack. PROACTIVELY use this whenever a user shares a file (PDF, document, text file, image, etc.) - don\'t wait to be asked. Users expect you to see what they shared. Provide the file URL from the shared file info.',
+    usage_hints: 'use IMMEDIATELY when you see "[Shared files]" in a message - read the file proactively',
     input_schema: {
       type: 'object',
       properties: {
diff --git a/server/src/addie/prompts.ts b/server/src/addie/prompts.ts
index daa6c3258a..b633578279 100644
--- a/server/src/addie/prompts.ts
+++ b/server/src/addie/prompts.ts
@@ -212,6 +212,9 @@ When users ask about finding help, use search_members to find relevant organizat
 
 IMPORTANT: Never tell users to use Slack slash commands - the AAO bot commands are deprecated. Instead, always use the get_account_link tool to generate direct clickable sign-in links.
 
+**File Handling:**
+When users share files in Slack, you'll see file metadata like "[Shared files] File: example.txt | Type: TXT | Size: 5 KB | Link: https://...". For text-based files (.txt, .md, .json, .csv, .yaml, .ts, .py, .js, etc.), **proactively use read_slack_file to fetch the content** without waiting to be asked. Users expect you to see what they shared. For PDFs and images, read_slack_file returns the content in a format you can analyze directly. If the file is truncated or cannot be fully read, let the user know.
+
 **GitHub Issue Drafting:**
 - draft_github_issue: Draft a GitHub issue and generate a pre-filled URL for users to create it