Odd behavior of Outlook365 SMTP and other problems...

Copper Contributor

For the past few weeks, I've been experiencing a few intermittent problems with getting authentication rejected by Office365.

I've got an office of around 20-25 seats. Most of the computers are running Win10, but all of the computers are running Office 2010. There are 3 computers in the network at this time which have legacy Win7 builds due to custom software that it is not cost effective to rebuild (approximate cost of around 40-60,000 USD to rebuild the software/server support). These three computers are generally not high usage, except for my own, which I keep in Win7 so I can continue to access and maintain the custom software (I am not the author, but I can keep it in line on the rare occasions it gives trouble).

Since around mid November, my own computer started to get some odd behavior and when I sent an email, I would get the "authentication rejected, try again" type popup.

I clicked OK 1-3 times and it would send the email fine. 

After a few weeks, suddenly it started giving me a nag screen every 2-7 seconds, which was really not fun and I had a chat with Tech support where we tried a handful of things, including removing the profile, building a new profile and all the normal stuff you would expect.

Of course it didn't actually work and while the frequency of the nag was reduced a bit, it continued popping up. I just carried on with the annoying nag. Fortunately, that was the end of the working day, so I didn't waste too much time, although I was admittedly quite annoyed.

And the next day, the problem had sort of magically disappeared. 

Since then, I occasionally get the popup of authentication rejected when sending an email, but I just click OK to retry a couple of times and it's fine.

So I believe this effectively eliminates the possibility that there's any issue with the individual user's computer or Win7 or even Office 2010. There's no profile corruption and the PST file is a manageable size.

So today, I've just been told that something similar is happening to one of our users on the special computers. I found that I needed to click 3-5 times to retry for emails being sent out. But that's all that was required. There is nothing actually wrong, just an issue with the SMTP server rejecting authorization for no obvious reason.

We did have a problem for a 3 separate users where the entire OneDrive account was wiped out, which was a problem that also resolved itself with no intervention after a few hours. We were able to determine that this was definitively a server-side problem, although we were not able to determine a cause, between the Malaysian Support Team, Nigerian Support Team, the Portugal Support Team and the UK Support Team. My account was one of the ones affected, but the user with the other computer affected by this problem does not use OneDrive functions so we don't know if there's anything related.

All I can say is that the Authorization rejected problem appears to not require any actual changes in order to send and receive emails, it just seems to fail auth a few times.

I just spoke to our local tech support team and they told me that they could not escalate to tech support because it is Office 2010. I told her that SMTP authentication is not client-based and will work the exact same in BlueMail, Thunderbird or any other POP client, so I do not accept that as an excuse. The SMTP server needs to work correctly *regardless* of what client is accessing it. The same goes for the OneDrive. It needs to work correctly, regardless of whether it's being accessed through a browser like Edge, Chrome, Firefox or Safari, through Teams or through the online version. The woman on the line flat out refused to create a ticket. Yeah, a woman in the billing team refusing to open a ticket for tech support over an issue she doesn't understand because she's not a trained tech support person. She's in the *BILLING* department.


I get it, it sounds like it could be a client issue, but we've literally been using this exact same setup for the last 3 years with Microsoft (longer than that overall, but for 3 full years while using Office365). And I have already gone over this thing with Tech Support a couple of months back and it was already ruled out that this is a problem with the client software.

It's almost like blaming us the customer because your server has glitches and then getting annoyed when we try to get support for when those glitches happen and we insist on actually getting support.

That team has dropped the ball for us so many times, failed to call back so many times, played absolute shenanigans with our account so many times over the past year, I've reached a level of frustration that I should never need to experience. This is the tip of the iceberg for me with the Malaysian Support Team. I know who the woman is. She's failed to give me callbacks on multiple occasions and she caused a huge problem with our billing that should have been solved in 30 seconds instead of the wildly convoluted solution she suggested (and got wrong twice, even when I told her specifically to make sure not to make that specific mistake). 

The Malaysian team doesn't actually have anyone on staff that works in tech support. They *only* have a billing department and they just write down details and create tickets which then get submitted to the global tech support group. Their managers will sometimes just stay home and not be available and can't be bothered to call back and on more than one occasion, I've had to comfort a girl who works there who has been literally crying because she doesn't know what to do because her English isn't great and she doesn't have a technical background and gets totally lost because she was never properly trained and doesn't even have an SOP for how to answer the phone properly. And when she looks around for a supervisor, there's nobody to help her. It's absolute insanity.

I have no recourse and I have tried to escalate with their oversight team as well and been completely ignored. 

I genuinely do not understand what is going on over there at Microsoft. It seems like nobody is actually in charge of this stuff and each individual support team is just doing whatever the heck they want.

I don't know why I can't just call in, report a problem and ask for a call-back to help troubleshoot it, especially when all available evidence looks like there's a problem at the account/server level. That's what I used to do and frankly, as much as Google is nowhere near as good as Microsoft, I've always been able to get good support from them.

I'm running out of options. I'm the guy who handles the decisions about tech and IT for our company and I'm the reason we switched to MS in the first place. I don't know what I'm supposed to do. I can't get basic tech support.

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