From d83beb2148ee079bdd7701c3f4c6d51638dd7383 Mon Sep 17 00:00:00 2001
From: Muhsin Keloth <muhsinkeramam@gmail.com>
Date: Thu, 2 Apr 2026 11:13:11 +0400
Subject: [PATCH] fix: Populate `extension` and include `content_type`  in
 attachment webhook payload (#13945)
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Attachment webhook event payloads (`message_created`) were missing the
file extension and content type. The `extension` column existed but was
never populated, and `content_type` was not included in the payload at
all.

## What changed

- Added `before_save :set_extension` callback to extract file extension
from the filename when saving an attachment.
- Added `content_type` (from ActiveStorage) to the `file_metadata` used
in `push_event_data`.

### Before
```json
{
  "extension": null,
  "data_url": "...",
  "file_size": 11960
}
```

### After
```json
{
  "extension": "pdf",
  "content_type": "application/pdf",
  "data_url": "...",
  "file_size": 11960
}
```

## How to reproduce
1. Send a message with a file attachment (e.g., PDF) via any channel
2. Inspect the `message_created` webhook payload
3. Observe `extension` is `null` and `content_type` is missing

🤖 Generated with [Claude Code](https://claude.com/claude-code)

---------

Co-authored-by: Claude Opus 4.6 (1M context) <noreply@anthropic.com>
---
 app/models/attachment.rb       |  9 ++++++++
 spec/models/attachment_spec.rb | 38 ++++++++++++++++++++++++++++++++++
 2 files changed, 47 insertions(+)

diff --git a/app/models/attachment.rb b/app/models/attachment.rb
index a1cc062a0..c6b4e1d80 100644
--- a/app/models/attachment.rb
+++ b/app/models/attachment.rb
@@ -37,6 +37,7 @@ class Attachment < ApplicationRecord
   belongs_to :account
   belongs_to :message
   has_one_attached :file
+  before_save :set_extension
   validate :acceptable_file
   validates :external_url, length: { maximum: Limits::URL_LENGTH_LIMIT }
   enum file_type: { :image => 0, :audio => 1, :video => 2, :file => 3, :location => 4, :fallback => 5, :share => 6, :story_mention => 7,
@@ -111,6 +112,7 @@ class Attachment < ApplicationRecord
   def file_metadata
     metadata = {
       extension: extension,
+      content_type: file.content_type,
       data_url: file_url,
       thumb_url: thumb_url,
       file_size: file.byte_size,
@@ -154,6 +156,13 @@ class Attachment < ApplicationRecord
     }
   end
 
+  def set_extension
+    return unless file.attached?
+    return if extension.present?
+
+    self.extension = File.extname(file.filename.to_s).delete_prefix('.').presence
+  end
+
   def should_validate_file?
     return unless file.attached?
     # we are only limiting attachment types in case of website widget
diff --git a/spec/models/attachment_spec.rb b/spec/models/attachment_spec.rb
index a17839174..5e1dd2107 100644
--- a/spec/models/attachment_spec.rb
+++ b/spec/models/attachment_spec.rb
@@ -187,6 +187,44 @@ RSpec.describe Attachment do
     end
   end
 
+  describe 'set_extension' do
+    it 'sets extension from filename on save' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('pdf')
+    end
+
+    it 'does not overwrite extension if already set' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file, extension: 'doc')
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      expect(attachment.extension).to eq('doc')
+    end
+
+    it 'handles filenames without extension' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake data'), filename: 'README', content_type: 'text/plain')
+      attachment.save!
+
+      expect(attachment.extension).to be_nil
+    end
+  end
+
+  describe 'push_event_data includes extension and content_type' do
+    it 'returns extension and content_type for file attachments' do
+      attachment = message.attachments.new(account_id: message.account_id, file_type: :file)
+      attachment.file.attach(io: StringIO.new('fake pdf'), filename: 'test.pdf', content_type: 'application/pdf')
+      attachment.save!
+
+      event_data = attachment.push_event_data
+      expect(event_data[:extension]).to eq('pdf')
+      expect(event_data[:content_type]).to eq('application/pdf')
+    end
+  end
+
   describe 'file size validation' do
     let(:attachment) { message.attachments.new(account_id: message.account_id, file_type: :image) }