# Pull Request Template
## Description
Large emails (2MB+ with multiple attachments) were causing IMAP email
processing jobs to timeout silently, blocking all subsequent emails from
being processed. This created an infinite loop where:
- Problematic emails were repeatedly fetched but never successfully
processed
- Other emails in the queue were never processed as we iterated
sequentially
- silent failures
### Solution
Enhanced the FetchImapEmailsJob with individual email processing
isolation:
### Key Changes
1. Individual Email Processing: Changed from map to each for better
memory efficiency
2. Timeout Protection: Added configurable timeout per email (default: 60
seconds)
3. Failure Tracking: Track failed emails with 6-hour expiry for retry
opportunities
4. Skip Logic: Skip emails that have failed 3+ times to prevent infinite
loops
5. Error Isolation: Each email is processed in its own error boundary
### Configuration
- Timeout: Configurable via EMAIL_PROCESSING_TIMEOUT_SECONDS using
GlobalConfigService
- Default: 60 seconds per email
- Failure Limit: 3 attempts before skipping
- Retry Window: 6 hours so that emails get 8 more chances in the 2 day
window
### Benefits
- Prevents queue blocking: One problematic email cannot stop others
- Maintains email order: Older emails (customers waiting longer)
processed first
- Automatic recovery: Failed emails get retry opportunities
- Better monitoring: Clear logging when emails timeout or are skipped
- Configurable: Deployments can adjust the timeout based on their needs
This fix ensures email processing reliability while maintaining existing
functionality.
## Type of change
Please delete options that are not relevant.
- [x] Bug fix (non-breaking change which fixes an issue)
- [x] New feature (non-breaking change which adds functionality)
- [ ] Breaking change (fix or feature that would cause existing
functionality not to work as expected)
- [ ] This change requires a documentation update
## How Has This Been Tested?
Please describe the tests that you ran to verify your changes. Provide
instructions so we can reproduce. Please also list any relevant details
for your test configuration.
## Checklist:
- [ ] My code follows the style guidelines of this project
- [ ] I have performed a self-review of my code
- [ ] 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
- [ ] 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
## Notion document
https://www.notion.so/chatwoot/Email-IMAP-Issue-30aa5f274c928062aa6bddc2e5877a63?showMoveTo=true&saveParent=true
## Description
PLAIN IMAP channels (non-OAuth) were silently retrying failed
authentication every minute, forever. When credentials are
wrong/expired, Net::IMAP::NoResponseError was caught and logged but
channel.authorization_error! was never called — so the Redis error
counter never incremented, reauthorization_required? was never set, and
admins were never notified. OAuth channels already had this handled
correctly via the Reauthorizable concern.
Additionally, Net::IMAP::ResponseParseError (raised by non-RFC-compliant
IMAP servers) was falling through to the StandardError catch-all,
flooding
Estimated impact before fix: ~70–75 broken IMAP inboxes generating
~700k–750k wasted Sidekiq jobs/week.
## Type of change
- [ ] Bug fix (non-breaking change which fixes an issue)
## Checklist:
- [ ] My code follows the style guidelines of this project
- [ ] I have performed a self-review of my code
- [ ] 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
- [ ] 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
Currently, auto-assignment runs only during conversation creation or
update events. If no agents are online when new conversations arrive,
those conversations remain unassigned.
With this change, unassigned conversations will be automatically
assigned once agents become available. The job runs every 15 minutes and
uses a fair distribution threshold of 100 to prevent a large number of
conversations from being assigned to a single available agent. This will
be customizable later.
### Snyk has created this PR to fix 1 vulnerabilities in the rubygems
dependencies of this project.
#### Snyk changed the following file(s):
- `Gemfile`
<details>
<summary>⚠️ <b>Warning</b></summary>
```
Failed to update the Gemfile.lock, please update manually before merging.
```
</details>
#### Vulnerabilities that will be fixed with an upgrade:
| | Issue | Score |
:-------------------------:|:-------------------------|:-------------------------
 | Web Cache Poisoning
<br/>[SNYK-RUBY-RACK-1061917](https://snyk.io/vuln/SNYK-RUBY-RACK-1061917)
| **616**
---
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[//]: #
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---------
Co-authored-by: snyk-bot <snyk-bot@snyk.io>
- Added a trait called microsoft_email for the Channel::Email factory.
- Rewrote the logic to make it simple to understand
- Rewrote the specs for readability
This allows a user to add/update a custom regex and a cue while defining custom attributes(Only applicable for type- text).
While adding/editing custom attributes, the values are validated against the attribute definition regex, and if it is incorrect, a cue message or default error message is shown and restricts invalid values from being saved.
Fixes: #6866
- Adds the backend APIs required for Microsoft Email Channels
Co-authored-by: Pranav Raj S <pranav@chatwoot.com>
Co-authored-by: Sojan <sojan@pepalo.com>
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
