Weird new problem with Gmail recipients of RS-sent emails...

[Douglas Thompson]

So, we've been using RS for years now with no Gmail issues, but all of a sudden we're getting some email "bouncebacks" from RS for Gmail address. Some are going through just fine, which is weird...

Anyway, the error message in the bouncebacks says:

"Messages missing a valid messageId header are not 550 5.7.1 accepted"

Like I said up top, this has worked fine for several years, so I suspect that something is in the process of changing with Gmail and something that has worked just fine all these years is suddenly now not enough to pass Gmail's muster.

Anyway, my question is...what can be done about this? I searched the Google Group for "messageID" and "email header" and "Gmail" to no avail.

Is there an alternative means of RS emailing that I need to set up, or some way to change what it includes in the headers of the email messages it sends out or something?

[Douglas Thompson]

Just had to share out some new photos via email and got a single "undeliverable" bounceback exactly like what I described earlier (complete with the same error message and whatnot) and was wondering if anyone had any insights...

[atc...@gmail.com]

I don't think there is anything ResourceSpace is necessarily doing which is causing the issue you are seeing. More likely that it has to do with your mail server configuration. If there are mail admins listening, please correct me if I am mistaken.

I would be curious if your domain has been properly configured with SPF. Without this configuration I could see Gmail "randomly" flagging these emails as spam or spoofed email messages or even bouncing messages. No guarantee that is it, but something worth investigating.

Microsoft SPF KB

https://docs.microsoft.com/en-us/microsoft-365/security/office-365-security/set-up-spf-in-office-365-to-help-prevent-spoofing?view=o365-worldwide

Google SPF KB

https://support.google.com/a/answer/33786?hl=en

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[Douglas Thompson]

I'll run this by our IS guy when I get the chance.

In the meantime, I've just had to share out some more photos via email and noticed that it's the same email addresses generating the "messageID not accepted" bouncebacks.

So it's not random.

The weird part is that, out of 45 users (or thereabouts), only five are misbehaving...

I've double-checked that the email addresses are entered correctly in our system and the bounceback stuff didn't start happening until a couple weeks ago...

It all smacks of Google changing something about Gmail and that has exposed something that was allowed to work previously but now isn't (although that doesn't explain why it works fine for the majority of our users...almost all of which have Gmail addresses btw)

[Douglas Thompson]

Well, I just had to share out some more photos via email and this time at least some of the bouncebacks were ones that worked fine previously, so maybe it is "random" what works and what doesn't...

Bottom line: any ideas about what this "Messages missing a valid messageId header are not 550 5.7.1 accepted" error is and how to go about fixing it (and if the fix is to somehow switch ResourceSpace to use a different email system than whatever it uses by default, then what do I need to do to that?)

[Mike Perry]

I think Jerry Beck has offered the most logical solution path.

It sounds as if the SMTP process of your RS server is introducing random errors in the mail headers to which GMail has issues. I would think comparing header contents between emails to GMail accounts that get bounced to emails to GMail accounts that have no issues might help track down the issue.

Just my .02 worth from a 30,000' view.

[Douglas Thompson]

Yeah I agree. I'm just throwing out new "data points" as I encounter them in case something triggers someone's memory as to another cause/culprit...preferably something that I can attempt to fix, as our IS people are currently (and have been for a couple weeks!) in an "all hands on deck" situation to resolve some campus network issues before classes start back up. So, the person who can usually help me with this stuff is currently not available, so I'm trying to find out as much as I can before I need to involve him.

Thanks for the info!

[Mike Perry]

No prob -- have a daughter in college. I know how hectic things can get a week or so before classes start. Grew up in the town where she goes to school, and understand college campus challenges real well!!!

[Douglas Thompson]

So just curious...what's the "$use_premailer=false;" line for in the RS config file? If I set that to "true", will that have any impact on this problem with random Gmail bouncebacks that we're having? Or will that just make things worse?

[reidb...@gmail.com]

Where are you seeing that config option? I just grep'd a whole install and don't see that anywhere...

[Douglas Thompson]

That may entirely be gone now...it was just in a GitHub repo of the config.default.php file. I don't currently have VPN access so I can take a look at our actual config.default.php file from here at home.

Just trying to figure out what my options are concerning this problem, so that when our IS guy becomes available (he and the other IS people are currently working on various "network woes"...hence my lack of VPN access) we can hopefully troubleshoot/eradicate the problem.

[Douglas Thompson]

Sorry I mistyped...it's "$use_phpmailer=false", and I just verified that it's in the confg.default.php file in our install...but, curiously, there's no documentation (not even comments around that line in the config.default.php file!) about it anywhere that I can find...

[Mike Perry]

It's called (and defined) in reporting_functions.php and several others.

https://www.resourcespace.com/knowledge-base/search.php?search=%24use_phpmailer

[Douglas Thompson]

Well, I spoke briefly with our IS guy, and it sounds like we're going to go whole-hog with this and switch RS to use a different SMTP server we have on campus to do its email-sending...so now I have to figure out what all config settings are involved in that...