I encountered what appears to be a mail-forwarding migration regression after upgrading from approximately Cloudron 9.2.0 to 10.0.1.
Before the upgrade, I had forwarding chains like:
address-a@example.com
→ address-b@example.com
→ external-recipient@example.net
Cloudron 10 migrated the former forwarding addresses into mailboxes with forwarding enabled, but these multi-stage chains no longer worked.
Mail sent to the first address was accepted and redirected to the second local mailbox, but never reached the external recipient. The messages remained in:
/home/yellowtent/boxdata/mail/haraka-queue
The queued messages confirmed that the first redirect occurred:
X-Sieve-Redirected-From: address-a@example.com
Delivered-To: address-a@example.com
After affected messages entered the queue, the entire mail service became unreliable. Roundcube reported:
SMTP Error (0): Connection to server failed.
Sending and receiving mail stopped working. Restarting the mail service did not resolve it because the problematic queue entries and forwarding configuration remained.
I recovered by:
- Moving the four stranded messages out of
haraka-queue.
- Changing each affected mailbox to forward directly to its final external recipient, eliminating the intermediate local forwarding mailbox.
- Restarting the mail service.
- Replaying the preserved messages through SMTP.
All replayed messages received SMTP 250 responses and appeared as Sent in Cloudron’s event log. New mail is also working normally.
Possible reproduction
- On Cloudron 9, create a forwarding address
A that forwards to another local forwarding address B.
- Configure
B to forward externally to C.
- Upgrade to Cloudron 10.0.1.
- Send mail to
A.
- Check whether it reaches
C or remains in haraka-queue.
It may also be reproducible directly on 10.0.1 by configuring forwarding-enabled mailboxes as:
A → B → external C
My suspicion is that the migration preserves each forwarding relationship without flattening the chain, while the new forwarding implementation does not safely handle mailbox-to-mailbox forwarding chains.