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rnwood / smtp4dev

smtp4dev - the fake smtp email server for development and testing
BSD 3-Clause "New" or "Revised" License
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MAIL FROM AUTH=<> returns 501 Parameter AUTH is not recognised #565

Open ddaymn opened 3 years ago

ddaymn commented 3 years ago

When sending mails using outlook they are rejected

250-AUTH=CRAM-MD5 PLAIN LOGIN ANONYMOUS 250 AUTH CRAM-MD5 PLAIN LOGIN ANONYMOUS MAIL FROM:outlook_28E0EB1540D65AC3@outlook.com SIZE=13343 AUTH=<> 501 Parameter AUTH is not recognised QUIT 221 Goodbye

rnwood commented 3 years ago

Hi. Thanks for reporting this.

Can you clarify which platform and version of Outlook this behaviour shows up with (or is this from web based outlook.com?). Also what settings do you have for the outgoing mail server authentication.

Thanks Rob

From: ddaymn notifications@github.com Sent: Thursday, November 19, 2020 7:54:53 PM To: rnwood/smtp4dev smtp4dev@noreply.github.com Cc: Subscribed subscribed@noreply.github.com Subject: [rnwood/smtp4dev] 501 Parameter AUTH is not recognised (#565)

When sending mails using outlook they are rejected

250-AUTH=CRAM-MD5 PLAIN LOGIN ANONYMOUS 250 AUTH CRAM-MD5 PLAIN LOGIN ANONYMOUS MAIL FROM:outlook_28E0EB1540D65AC3@outlook.commailto:outlook_28E0EB1540D65AC3@outlook.com SIZE=13343 AUTH=<> 501 Parameter AUTH is not recognised QUIT 221 Goodbye

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ddaymn commented 3 years ago

It is outlook.com in general. My thought is that it is the empty AUTH<> I see other messages that work but there are values in between the <>. That value above was from the session log in smtp4dev. I do not have SMTP relay enabled.

rnwood commented 3 years ago

I've had a look at web based Outlook (there's several apps branded as this by MS).

Can you confirm you are referring to the app at https://outlook.live.com/ (not the O365 one at outlook.office.com) and specifically that this can be reproduced using these settings to get it to send outgoing messages via SMTP: image

GeoMaciolek commented 3 months ago

I'm happy to work to troubleshoot this - I'm noticing, this seems to occur when we're using Exchange Online mail routing rules to Redirect a message to this server - sending email directly from the same Office/MS 365 Tenant works fine.

Noting in this case - running on Port 25. default settings, and no MX records; mail was sent to an address like user@asubdomain.mypersonaldomain.com.

GeoMaciolek commented 3 months ago

Here's the session log from the session in question!

220 my.public.hostname smtp4dev ready
EHLO NAM11-BN8-obe.outbound.protection.outlook.com
250-Nice to meet you.
250-8BITMIME
250-SIZE
250-SMTPUTF8
250-AUTH=CRAM-MD5 PLAIN LOGIN
250 AUTH CRAM-MD5 PLAIN LOGIN
MAIL FROM:<bouncesEtr+SRS=8Wfmu=OI=outlook.com=my@employer.com> SIZE=41816 AUTH=<>
501 Parameter AUTH is not recognised
QUIT
221 Goodbye