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[GH-ISSUE #558] v1.27.6 HELO/EHLO Issue with M365 #359
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Originally created by @kjake on GitHub (Aug 25, 2025).
Original GitHub issue: https://github.com/axllent/mailpit/issues/558
Updated to v1.27.6 and now relaying to Exchange Online / Microsoft 365 has stopped working:
msg="[relay] error: error saying HELO/EHLO to [redacted].mail.protection.outlook.com:25: smtp: Hello called after other methods"@kjake commented on GitHub (Aug 25, 2025):
Rolled back to v1.27.5, exported messages and then ingested and they're relaying appropriately now.
@axllent commented on GitHub (Aug 25, 2025):
Oh no, that's unfortunate. This is definitely related to a recent change submitted by @petek. Pete, any ideas? This error originates within the Go SMTP client if Helo has already been called earlier on in the transaction (or maybe connection).
@petek commented on GitHub (Aug 25, 2025):
Moving the HELO block above the STARTTLE block should fix the error.
According to protocol, STARTTLS is supposed to reset the connection, hence why the HELO should go there. But it appears the client does not agree and moving the block may be necessary.
@axllent commented on GitHub (Aug 25, 2025):
Thank you for your input @petek. I suspect you are correct (
StartTLS()sets this if it hasn't already been set here), although the only way to be 100% sure is to test this.If I was to make a change to address this, would you both be able to test this for me to confirm it works with the relay services, before I do any future Mailpit releases? This would mean you would both have to test with the
axllent/mailpit:edgeDocker image after I made the change.@kjake commented on GitHub (Aug 25, 2025):
Yes! It wouldn't be hard for me to test that.
fwiw, I do have
starttls: truein my relayconfig.@axllent commented on GitHub (Aug 26, 2025):
I have pushed the change to the
developbranch (which is used to build the edge docker image). @kjake & @petek - please could you both test using the latestaxllent/mailpit:edgebuild and confirm this works for both of you (ie: Google & MS relay services)? Thank you.@petek commented on GitHub (Aug 26, 2025):
This has worked for me in my local environment. @axllent @kjake
@kjake commented on GitHub (Aug 26, 2025):
Worked here too!
Using
axllent/mailpit:edge@sha256:52ac6714e0e572bda3ff3ad5282b4e76db005c882ccbb85ea511329f8e87796b:@axllent commented on GitHub (Aug 27, 2025):
Thank you both for testing & confirming. I have just released the patch fix for this in v1.27.7 (currently no difference to the edge build you just tested).