Inbound emails containing null bytes could fail while Chatwoot persisted
the incoming message, causing IMAP sync to drop and repeatedly retry the
same malformed email. This strips null bytes at the inbound mailbox
message persistence boundary so the rest of the email can be saved
normally.
Fixes
https://linear.app/chatwoot/issue/CW-7165/argumenterror-string-contains-null-byte-argumenterror
Sentry: https://chatwoot-p3.sentry.io/issues/7405946944/
## Test
- [x] added specs
- [x] manually tested the logic on prod for the inbox(email) which was
throwing the error
## What changed
- Sanitizes null bytes only while building attributes for inbound
mailbox message persistence.
- Uses the sanitized source ID for both duplicate lookup and message
creation.
- Adds regression coverage for the mailbox message creation path.
---------
Co-authored-by: Sony Mathew <2040199+sony-mathew@users.noreply.github.com>
Co-authored-by: Sony Mathew <sony@chatwoot.com>
## Description
Inbound email attachments are stored with `file_type: 'file'` regardless
of their actual MIME type. As a result, image screenshots shared by
customers via email are not exposed to Captain V2's multimodal pipeline
— `Captain::OpenAiMessageBuilderService#attachment_parts` selects images
via `attachments.where(file_type: :image)` and emits a placeholder
`"User has shared an attachment"` text part instead of an `image_url`
part. The model never gets the image, so Captain keeps asking the
customer to retype information that is already visible in the
screenshot.
This PR makes the email mailbox derive `file_type` from the blob's
`content_type` using the existing shared `FileTypeHelper`, matching how
every other inbound channel (`twilio`, `sms`, `telegram`, `line`,
`tiktok`, `twitter`, `messenger`) and `MessageBuilder` already classify
attachments.
Fixes#14448
## Type of change
- [x] Bug fix (non-breaking change which fixes an issue)
## How Has This Been Tested?
Reproduced and verified on a self-hosted production instance:
1. Real customer reply via email with a PNG screenshot of an in-app
error.
Before:
```ruby
a = Message.find(<id>).attachments.first
a.file_type # => "file"
a.file.blob.content_type # => "image/png"
Captain::OpenAiMessageBuilderService.new(message:
a.message).generate_content
# => [{type: 'text', text: '...'},
# {type: 'text', text: 'User has shared an attachment'}] ❌ no image_url
```
Captain reply: "Please copy and paste the full error text…" (model never
saw the image).
2. After the patch + force-recreate, same conversation:
```ruby
a.file_type # => "image"
Captain::OpenAiMessageBuilderService.new(message:
a.message).generate_content
# => [{type: 'text', text: '...'},
# {type: 'image_url', image_url: {url: 'https://.../<blob>.png'}}] ✅
```
Captain reply now correctly references the on-screen error text from the
screenshot via the multimodal vision path — no more deflection.
3. Regression sanity-check on non-image attachments (PDF / Office docs):
`file_type` falls through to `:file`, behavior unchanged.
## Notes for self-hosted operators
Existing email image attachments in the DB will still have `file_type:
'file'`. A one-shot backfill is straightforward and safe (no data loss,
only metadata):
```ruby
Attachment.joins(message: :conversation)
.where(messages: { content_type: 'incoming_email' })
.where(file_type: 'file')
.find_each do |a|
next unless a.file.attached?
ct = a.file.blob.content_type.to_s
next unless ct.start_with?('image/', 'audio/', 'video/')
new_type = ct.start_with?('image/') ? :image : (ct.start_with?('video/') ? :video : :audio)
a.update_columns(file_type: Attachment.file_types[new_type])
end
```
## Checklist
- [x] My code follows the style guidelines of this project
- [x] I have performed a self-review of my code
- [x] My changes generate no new warnings
- [ ] I have added tests that prove my fix is effective — happy to add a
`mailbox_helper_spec` example for `process_regular_attachments` if
maintainers prefer; existing specs in that file focus on inline-image
handling.
---------
Co-authored-by: Aakash Bakhle <48802744+aakashb95@users.noreply.github.com>
## Description
This pull request addresses issue #11948, where inline images embedded
in emails (such as those sent from Outlook) are not rendered correctly
if the Content-Disposition header is missing.
The solution ensures that images referenced via cid: in the HTML body
are correctly identified and rewritten using url_for.
Fixes#11948
## Type of change
Bug fix (non-breaking change which fixes an issue)
## How Has This Been Tested?
Added test: detects image inline attachment by cid reference when
Content-Disposition is missing
## Checklist:
- [X] My code follows the style guidelines of this project
- [X] I have performed a self-review of my code
- [X] I have commented on my code, particularly in hard-to-understand
areas
- [ ] I have made corresponding changes to the documentation
- [ ] My changes generate no new warnings
- [X] I have added tests that prove my fix is effective or that my
feature works
- [ ] New and existing unit tests pass locally with my changes
- [ ] Any dependent changes have been merged and published in downstream
modules
---------
Co-authored-by: Pranav <pranav@chatwoot.com>
Co-authored-by: Sojan Jose <sojan@pepalo.com>
Co-authored-by: Sony Mathew <sony@chatwoot.com>
Co-authored-by: Sony Mathew <2040199+sony-mathew@users.noreply.github.com>
While investigating a customer-reported issue, I found that some emails
were appearing late in Chatwoot. The root cause was query timeouts.
It only happened for emails with an in_reply_to header. In these cases,
Chatwoot first checks if a message exists with message_id = in_reply_to.
If not, it falls back to checking conversations where
additional_attributes->>'in_reply_to' = ?.
We were using:
```rb
@inbox.conversations.where("additional_attributes->>'in_reply_to' = ?", in_reply_to).first
```
This looked harmless, but .first caused timeouts. Without .first, the
query ran fine. The issue was the generated SQL:
```sql
SELECT *
FROM conversations
WHERE inbox_id = $1
AND (additional_attributes->>'in_reply_to' = '<in-reply-to-id>')
ORDER BY id ASC
LIMIT $2;
```
The ORDER BY id forced a full scan, even with <10k records.
The fix was to replace .first with .find_by:
```rb
@inbox.conversations.find_by("additional_attributes->>'in_reply_to' = ?", in_reply_to)
```
This generates:
```sql
SELECT *
FROM conversations
WHERE inbox_id = $1
AND (additional_attributes->>'in_reply_to' = '<in-reply-to-id>')
LIMIT $2;
```
This avoids the scan and runs quickly without needing an index.
By the way, Cursor and Claude failed
[here](https://github.com/chatwoot/chatwoot/pull/12401), it just kept on
adding the index without figuring out the root cause.
Co-authored-by: Muhsin Keloth <muhsinkeramam@gmail.com>
The term "sorcerer’s apprentice mode" is defined as a bug in a protocol
where, under some circumstances, the receipt of a message causes
multiple messages to be sent, each of which, when received, triggers the
same bug. - RFC3834
Reference: https://github.com/chatwoot/chatwoot/pull/9606
This PR:
- Adds an auto_reply attribute to message.
- Adds an auto_reply attribute to conversation.
- Disable conversation_created / conversation_opened event if auto_reply
is set.
- Disable message_created event if auto_reply is set.
---------
Co-authored-by: Muhsin Keloth <muhsinkeramam@gmail.com>
Add bounced emails to the conversation thread.
Fix Gmail bounce detection by checking the X-Failed-Recipients header.
Currently, bounced emails are rejected as auto-replies, which causes
support agents to miss important delivery failure context. This PR
ensures bounced messages are correctly added to the thread, preserving
visibility for the support team.
In Chatwoot, we rely on the Content-ID for inline attachments to replace
the link with the uploaded attachment URL. Our expectation was that only
images would be inline, while other attachments would not. However,
email clients like Apple Mail (sigh) allow users to send inline
attachments that are not images, and these attachments often lack a
Content-ID. This creates significant issues in rendering.
I investigated how other email clients handle this scenario. When
viewing the same email (sent from Apple Mail) in Gmail, only one image
appears—and it’s treated as an attachment, not inline. This happens
because both attachments are the same image, and Apple Mail only sends
one copy. See the screenshot below.
| Apple Mail | Gmail |
| -- | -- |
| <img width="646" alt="Screenshot 2025-02-27 at 8 20 17 PM"
src="https://github.com/user-attachments/assets/e0d1cd2d-e47c-4081-a53b-7a67106341b3"
/> | <img width="360" alt="Screenshot 2025-02-27 at 8 20 51 PM"
src="https://github.com/user-attachments/assets/b206e56e-8f86-43e9-867b-d895c36aff78"
/> |
A good fix for this would be to check if the Content-ID is missing and
then upload the file as a regular attachment. However, the Mail gem (for
some reason) automatically adds a default Content-ID to inline parts. I
need to dig into the source code to understand why this happens.
For now, I’ve implemented a check to treat non-image attachments as
regular attachments. Inline image attachments are already handled by
appending an image tag at the end if the content-id is not found in the
body. A sample conversation to test this behavior is
[here](https://app.chatwoot.com/app/accounts/1/conversations/46732).
Some email clients automatically set Content-Disposition to inline for
specific content types, such as images. In cases where the email body is
empty, inline attachments may not display correctly due to our previous
implementation. Our assumption was that these attachments are referenced
within text/plain or text/html parts.
Customer-reported issues, especially with Apple Mail, show emails with
attachments marked as inline but without any corresponding text parts.
This leads to missing attachments even though would have processed the
attachment.
This update introduces a check for the presence of a text part. If none
exists, inline attachments are treated as regular attachments and added
to the external attachments array, ensuring that all attachments display
properly.
<details>
<summary><b>Script to update the existing emails that are already
available in the system</b></summary>
```rb
def update_content id
message = Message.find id
conversation = message.conversation
message_id = message.source_id
channel = message.inbox.channel
authentication_type = 'XOAUTH2'
imap_password = Google::RefreshOauthTokenService.new(channel: channel).access_token
imap = Net::IMAP.new(channel.imap_address, port: channel.imap_port, ssl: true)
imap.authenticate(authentication_type, channel.imap_login, imap_password)
imap.select('INBOX')
results = imap.search(['HEADER', 'MESSAGE-ID', message_id])
message_content = imap.fetch(results.first, 'RFC822').first.attr['RFC822']
mail = MailPresenter.new(Mail.read_from_string(message_content))
mail_content = if mail.text_content.present?
mail.text_content[:reply]
elsif mail.html_content.present?
mail.html_content[:reply]
end
attachments = mail.attachments.last(Message::NUMBER_OF_PERMITTED_ATTACHMENTS)
inline_attachments = attachments.select { |attachment| attachment[:original].inline? && mail_content.present? }
regular_attachments = attachments - inline_attachments
regular_attachments.each do |mail_attachment|
attachment = message.attachments.new(
account_id: conversation.account_id,
file_type: 'file'
)
attachment.file.attach(mail_attachment[:blob])
end
message.save!
end
```
</details>
* fix: downcase email when finding
* feat: add `from_email` class
* refactor: use `from_email`
* feat: add rule to disallow find_by email directly
* chore: remove redundant test
Since the previous imlpmentation didn't do a case-insentive search, a new user would be created, and the error would be raised at the DB layer. With the new changes, this test case is redundant
* refactor: use from_email
* fix: change email conversation not found exception to log
* chore: refactor reply_mailbox methods
---------
Co-authored-by: Sojan Jose <sojan@pepalo.com>
Refactor code in ApplicationMailbox
* short-circuiting as soon as we get a "true" value in some cases
* using ".exists?" instead of instantiating an ActiveRecord object
* using "match?" instead of "match"
This change allows the user to configure both IMAP and SMTP for an email inbox. IMAP enables the user to see emails in Chatwoot. And user can use SMTP to reply to an email conversation.
Users can use the default settings to send and receive emails for email inboxes if both IMAP and SMTP are disabled.
Fixes#2520
Configuring an agent email also as a support email inbox leads to conversations getting created in a loop if notifications were also configured to the same email.
For emails forwarded from google groups, Google rewrites the FROM address to the group email and the original email will be available under X-Original-Sender. This PR enables chatwoot to handle this case.
Fixes: #2715
