ISPConfig Roundcube Out of Office Reply / Vacation Message - Error 550: Empty envelope Sender

Hi all, wondering if anyone else has or had this issue. Can't seem to find much on how one would solve this.
I recently installed the ispconfig plugins for RoundCube. (set them up easily enough). I sent a test message to the email address with the enabled out of office reply. The server sent a message back, however, it stops short of getting all the way to the original sender. The mail server blocks the return reply with the notice below:

to=<[email protected]>, relay=spamfilter.email.com[88.88.88.88]:587, delay=1.6, delays=0.28/0.02/1.3/0.07, dsn=5.0.0, status=bounced (host spamfilter.email.com[88.88.88.88] said: 550 Empty envelope senders not allowed (in reply to DATA command))
Jan 2 21:17:09 ns1 postfix/qmgr[28010]: DA3B868C0795: removed

I can only assume that Roundcube is not attaching a sender email address when responding with the notice.
Does anyone know what I can do to make Roundcube include that information in the return reply?

Thank you so much in advance!
Best regards, and happy new years everyone!!

 

Thanks Th0m for your response, I used these instructions for Debian, though i am using Ubuntu 18.04.5 LTS (Bionic Beaver)) with ISPConfig 3.1dev

https://www.howtoforge.com/tutorial/ispconfig-3-roundcube-plugins-on-debian-stretch/
I setup the Autoreply with the few fields that are available. Set date start and end.. and save it.

 

Thanks for your response Norel, the receiving side is using Barracuda spamfilter and is set to not receive messages without the sender email included within the envelope. It's probably a good thing from the receiving side not to allow such messages in order to reduce the amount of spam and malware. That said, I think the sending side should have the ability to include this when replying with the "out of office" message... no?

 

I'm not familiar with the RFC's. I just assumed that there would be an option to enable the sender in the response, I just couldn't find it, that is the reason for my post.

This is exactly what I needed to get around the existing issue!! I will research the RFC to see that I don't break anything.
Thank you so much Jesse!!

 

Hi guys, so many years ago, I'm still having an issue with this. Apparently, GMAIL is now enforcing rules so that incoming mail gets dropped with there is no Envelope Sender. Any help would be appreciated.

 

Well, it may be a bit more complicated then original thought. The autoresponder sends out a vacation message as seen in postfix like this:

When google receives the message, it instantly rejects it with this:

The x.x.x.x is indeed in the SPF record and I've tested the DKIM which passes. If I send a normal email to gmail it works fine.

Really hoping someone can chime in on this.
Thank you!!

 

It fails. The RFC for SPF describes that if the envelop-from field is missing from an email, which is the case here, the spf validation falls back to the "client helo" your clients e.g. your mailserver domian most likly has no spf record present so it fails as google requires spf.

 

I can confirm the mail is getting through now, but is always tagged as JUNK and moves directly to JUNK folder. (only as a autoresponse, not as a direct message). I assume that is because it now passes SPF. I'm thankful at least that the mail is getting through, but is there a way to avoid getting tagged? Any way to have the autoresponder mechanism know to include the :FROM envelope sender and not leave it blank?

When the message comes in... it seems only logical that the autoresponder should include a envelope sender of the user that the message was destined to. Is there a way to tell it to?

 

Are you guys having similar issue or is this just because I'm sending mail through a relayhost?

 

I will install a new ISPConfig and setup Amavis and all the other features. Then try again. I can't get the outgoing mail to be signed with DKIM with my initial implementation. -- I'll update the forum with my results. Thanks Till!

 

Oh, really. I created a new server with Amavis and it does indeed sign the outgoing email with DKIM. Will Rspamd, do same? I installed 20.04/Ubuntu. Is the new version on 22.04?

 

Sweet!! Do you know if either will have ARC embedded. I don't know much about it, but it seems that ARC will allow us to forward mail on behalf of others and keep the DMARC/DKIM/SPF pass information intact.