# Pull Request Template
## Description
Prevent deleted email conversations from being synced into Chatwoot
again while they are still within the IMAP sync window.
When an admin explicitly deletes an email conversation, the incoming
email message IDs are stored temporarily in Redis. IMAP sync checks
these recently deleted message IDs in addition to existing message
records. Each Redis key expires automatically after two days.
This applies only to explicit conversation deletion. Individual message
deletion, inbox deletion, and account deletion keep their existing
behavior.
Fixes
[CW-7214](https://linear.app/chatwoot/issue/CW-7214/deleted-mails-in-gmail-inbox-gets-synced-again)
Fetch IMAP message content using `BODY.PEEK[]` instead of `RFC822` to
avoid provider-specific parser failures while preserving unread state.
This also applies the existing SMTP timeout configuration to custom SMTP
email-channel replies, so provider SMTP responses have enough time to
complete.
Fixes: https://github.com/chatwoot/chatwoot/issues/12762
## Why
Some IMAP providers can return responses for `FETCH RFC822` that Ruby
`net-imap` fails to parse with:
`Net::IMAP::ResponseParseError: unexpected RPAR (expected ATOM or NIL)`
We reproduced this with iCloud IMAP. Authentication, `INBOX` selection,
and header fetches worked, but fetching full message content with
`RFC822` failed before Chatwoot received a `Mail::Message`.
The same mailbox successfully returned full message content when fetched
with `BODY.PEEK[]`.
> During end-to-end iCloud validation, inbound fetch worked after the
IMAP change, but outbound replies through the custom SMTP settings could
still fail with a socket read timeout. The OAuth SMTP path already used
explicit SMTP timeout values; the custom SMTP path was relying on mailer
defaults instead.
## What this change does
- Replaces the full message fetch from `RFC822` to `BODY.PEEK[]`
- Reads the returned message content from `BODY[]`, which is how
`net-imap` exposes the response attribute
- Keeps the existing `BODY.PEEK[HEADER]` header-fetch behavior unchanged
- Applies `SMTP_OPEN_TIMEOUT` and `SMTP_READ_TIMEOUT` to custom SMTP
email-channel replies
- Defaults custom SMTP reply delivery to `open_timeout: 15` and
`read_timeout: 30`
- Updates IMAP service specs for standard and Microsoft IMAP fetch flows
- Updates mailer specs for custom SMTP timeout settings
`BODY.PEEK[]` is preferable here because it fetches the full message
content without marking messages as read.
## Validation
- Configured a local email inbox against iCloud IMAP and SMTP
- Confirmed `FETCH RFC822` reproduces `Net::IMAP::ResponseParseError:
unexpected RPAR (expected ATOM or NIL)`
- Confirmed `BODY[]` and `BODY.PEEK[]` fetch the same mailbox
successfully
- Confirmed Chatwoot imports iCloud messages after the IMAP change
- Sent two outbound replies from the Chatwoot UI through iCloud SMTP
after applying the timeout settings
- Confirmed both UI-created outbound messages were marked `sent`, had
iCloud SMTP `source_id` values, and had no `external_error`
- Ran `bundle exec rspec spec/services/imap/fetch_email_service_spec.rb
spec/services/imap/microsoft_fetch_email_service_spec.rb`
- Ran `bundle exec rspec spec/mailers/conversation_reply_mailer_spec.rb`
# Pull Request Template
## Description
This PR adds IMAP authentication mechanism selection to Chatwoot's email
inbox configuration. Users can now choose between 'plain', 'login', and
'cram-md5' authentication methods when configuring IMAP settings,
providing flexibility for different email providers that require
specific authentication types.
https://github.com/chatwoot/chatwoot/issues/8867
The implementation includes:
- Frontend dropdown with numeric keys (1, 2, 3) matching SMTP auth style
- Backend API validation for allowed authentication mechanisms
- Consistent 'cram-md5' format throughout the codebase
- Updated IMAP service to handle different auth types properly
This feature maintains consistency with existing SMTP authentication
options and follows the established UI/UX patterns in the application.
## Type of change
Please delete options that are not relevant.
- [x] New feature (non-breaking change which adds functionality)
- [ ] Bug fix (non-breaking change which fixes an issue)
- [ ] 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?
### Manual Testing:
- Tested in Docker environment
- Verified IMAP auth dropdown appears in inbox settings
- Confirmed all three auth mechanisms (plain, login, cram-md5) can be
selected and saved
- Tested API validation by attempting to save invalid auth mechanisms
### Automated Testing:
- Updated existing IMAP service tests to use consistent lowercase values
- Updated API controller tests for authentication parameter handling
- All tests pass locally with the new changes
### Test Configuration:
- Tested with both new and existing inbox configurations
## 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
- [x] I have made corresponding changes to the documentation
- [x] My changes generate no new warnings
- [x] I have added tests that prove my fix is effective or that my
feature works
- [x] New and existing unit tests pass locally with my changes
- [x] Any dependent changes have been merged and published in downstream
modules
## Additional Notes
- This feature is backward compatible and doesn't break existing IMAP
configurations
- The 'cram-md5' format is used consistently throughout (UI, API,
storage, services)
- Net::IMAP compatibility is maintained by converting to 'CRAM-MD5'
internally
- Follows the same pattern established by SMTP authentication
configuration
---------
Co-authored-by: João Santos <joao.santos@madigital.eu>
Co-authored-by: Sony Mathew <sony@chatwoot.com>
This PR limits IMAP email fetching to 500 messages per sync run to avoid
expensive/long-running mailbox scans. It also filters out
already-imported emails and Chatwoot-generated notification emails
during the header fetch phase, before fetching full email bodies,
reducing unnecessary IMAP work.
Fixes #CW-7001 (issue) :
https://linear.app/chatwoot/issue/CW-7001/emails-not-syncing
