Outlook and IMAP

[carmen617]

I've said it for years.....Outlook is first and foremost designed to be an email client to Exchange. The email, contacts, calendar, signatures...all the data is stored in the users Exchange mailbox. The computer is disposable, nothing needs to be backed up. Setup another computer and it's all there, calendar, contacts, email, signature, etc. Everything is fully equal on all devices..as designed...works great.

residential grade email POP/IMAP support was partially added to Outlook later, as an afterthought, but...it stinks. Outlook with IMAP stinks...avoid it at all costs.

residential grade email..stick to web browser access.
Outlook...use it for Microsoft 365.

...or...deal with constant headaches.

All well and good, but plenty of people do use it, and are comfortable with it, and want to use it - especially people who have used it for work, and want to access more than one email account in a single place, with a single contact list, etc. The inclusion of Outlook is a major reason home users choose to buy a Microsoft 365 subscription rather than just buying a one-time Home and Student license.

I've been living with the issues, and warn my clients about the issues - but, as this thread has evolved, it's clear some people have more issues than others. There might be some magical settings that make it work better - it seems worthwhile to see if anybody has suggestions.

 

[britechguy]

it's clear some people have more issues than others. There might be some magical settings that make it work better - it seems worthwhile to see if anybody has suggestions.

I really don't know whether these issues are "on the Outlook end" versus "on the email server end" or a combination of those two for certain services.

I'm one of those people who have not only had few, but no, issues with Outlook and IMAP. I don't use Outlook regularly myself, though I do have it configured on my machine with two Gmail accounts using IMAP, with never a bobble here, and I have lots of residential clients and very small business clients who use Outlook with IMAP without issue.

It would be interesting to finally get to the root of what it is that actually causes the issues with IMAP when those do occur. It makes no sense that any modern email client cannot handle all email protocols that remain in support and with wide availability with grace. They kinda have to.

 

[Markverhyden]

Microsoft hasn't updated that part of the program. I can assure you, that's an error message from O365.

Yep. I've seen it that style dialog box on several customers dealing with other things related to sending/receiving errors. There's more "legacy" stuff hanging around like Control Panel. I'm guessing these are items they're planning on deprecating in the near future.

 

[carmen617]

Out of curiosity if you go to outlook connection status are the servers in a disconnected state? Does clicking reconnect force them to connect successfully?

OK, after working fine for the first half of today, I got another dropped connection, so I checked the connection status windows. Shows a blank, as pictured. And Outlook has thrown the normal error. But also, you can see that Outlook in the lower right reports itself as "connected". Clicking "reconnect" pops up attempts to connect to my email accounts but then it goes blank again with no error message. Maddening.

 

[britechguy]

@carmen617

Is the client truly wed to using Outlook? The only reason I ask is that it is entirely possible that you will not reach a satisfactory conclusion in your pursuit.

If they are not wed to Outlook, and depending on how many e-mail accounts they have, there are a number of other email client options available that seem to have zero issues with IMAP access, ever.

The client may be more inclined to go the "new email client" route if you explain that this issue may not have a resolution under Outlook.

 

[britechguy]

@carmen617

Something just occurred to me that I hadn't thought of, but what polling interval do you have Outlook using for automatic send/receive? In the modern ones (at least from Outlook 2016 forward) Microsoft made the default 30 minutes, which is insanely long in my opinion.

I have my polling interval set to 10 minutes or less, depending on the situation, but I don't think I've ever set it to more frequent than every 5 minutes, though I know someone using every 1 minute.

If you haven't changed this, see: Changing the Send/Receive interval in Outlook (all modern versions, and perhaps earlier ones)
or this post on the JAWS Group of Groups.io. It's two different roads to the same destination. Both are written with a blind audience in mind, but the sighted can use keyboard shortcuts instead of point and click.

 

[Markverhyden]

So I just had a thought, yes I know that's dangerous, @carmen617. I don't recall you mentioning it so have you looked at event viewer when this happens. Maybe there's some underlying OS/system related issue that the Outlook errors aren't reflecting.

 

[Sky-Knight]

OK, after working fine for the first half of today, I got another dropped connection, so I checked the connection status windows. Shows a blank, as pictured. And Outlook has thrown the normal error. But also, you can see that Outlook in the lower right reports itself as "connected". Clicking "reconnect" pops up attempts to connect to my email accounts but then it goes blank again with no error message. Maddening.

View attachment 13662

This happens when you have a proxy on your system mucking with mail protocols, this is most typically due to 3rd party AV especially something involving a firewall. If it says "internet security" it needs to die in a fire!

Also, try outlook.exe /safe in the run box, if it works in safemode, and it doesn't work normally that's further evidence you've got a 3rd party plugin of some sort mucking with Outlook. The connection errors are distinct... they mean exactly what they claim, Outlook cannot contact the server in question. WHY is a brutal mess, but that's a network problem not a software problem but in this case Outlook has its own plugin mess before it can even get to the network, which merges the two realities.

And the worst thing? Malware lives in this world too... working as IMAP / POP3 / HTTP and HTTPS proxies...

 

[britechguy]

@Sky-Knight

Not that I don't believe what you've said, because I know it to be absolutely true, but I have seldom seen this kind of wide variablilty with the sorts of issues you mention. It tends to be more of an "all or nothing"/"works or consistently doesn't work" affair. The mucking is constant or it's not there kinda thing.

That's what strikes me as very odd here.

 

[Sky-Knight]

@britechguy Because Internet!

Outlook is just another thing looking up a web address and then making a connection to a service as configured. The problem is we have 80 11 bazillion differing things that interfere with that specific mechanism all in the name of content control. This control can be leveraged for antimalware purposes, as well as many other things.

So when I have a user show up with consistent Outlook issues, the first thing I do is yank the 3rd party AV because in most cases it clears the error permanently. I have no idea why some AV's proxies can get into a state where it'll work one moment and not the next, and I honestly do not care. That entire mechanism is simply rife for failure, and my greying and receding hair no longer has the patience for such insanity.

Also, less commonly I've seen ISPs muck with egress mail too, because there's a HORDE of botnet activity in this space that vendors are trying to control. There are truly countless reasons why that specific error can happen, which is why the Googling of that code is all but useless. You have to troubleshoot the entire connection chain between outlook and the server it's connecting to, and you simply do not have the visibility to see all of it!

Finally.... DNS... we haven't even gone there and it's always a problem too. For all of the above reasons and so many more.

 

[carmen617]

@carmen617

Is the client truly wed to using Outlook? The only reason I ask is that it is entirely possible that you will not reach a satisfactory conclusion in your pursuit.

If they are not wed to Outlook, and depending on how many e-mail accounts they have, there are a number of other email client options available that seem to have zero issues with IMAP access, ever.

The client may be more inclined to go the "new email client" route if you explain that this issue may not have a resolution under Outlook.

In this case, I am the client - this is my own system I am dealing with, and I want it to work. And yes, I am married to Outlook - I like using it to manage my business contacts (I have over 1500 of them in there) and I support enough clients who use Outlook that I need to be comfortable with it, especially as Microsoft mucks it up with updates. These disconnects have always happened, but they are now a daily event, rather than an every other week event. It's unacceptable.

 

[carmen617]

This happens when you have a proxy on your system mucking with mail protocols, this is most typically due to 3rd party AV especially something involving a firewall. If it says "internet security" it needs to die in a fire!

Also, try outlook.exe /safe in the run box, if it works in safemode, and it doesn't work normally that's further evidence you've got a 3rd party plugin of some sort mucking with Outlook. The connection errors are distinct... they mean exactly what they claim, Outlook cannot contact the server in question. WHY is a brutal mess, but that's a network problem not a software problem but in this case Outlook has its own plugin mess before it can even get to the network, which merges the two realities.

And the worst thing? Malware lives in this world too... working as IMAP / POP3 / HTTP and HTTPS proxies...

There is no proxy on my system, I am using Windows Defender, and this particular system, which is a high end Dell, is about 6 months old and has never had a third party AV on it. There are no plug ins beyond what Microsoft sticks on Outlook. My system is not infected with malware.

 

[carmen617]

So I just had a thought, yes I know that's dangerous, @carmen617. I don't recall you mentioning it so have you looked at event viewer when this happens. Maybe there's some underlying OS/system related issue that the Outlook errors aren't reflecting.

I've never had much luck tracking things down in event viewer, but I'll give it a look, thanks!

 

[DRPCNZ]

EM Client as possible alternative? Lol.

+1

 

[Markverhyden]

There is no proxy on my system, I am using Windows Defender, and this particular system, which is a high end Dell, is about 6 months old and has never had a third party AV on it. There are no plug ins beyond what Microsoft sticks on Outlook. My system is not infected with malware.

View attachment 13663View attachment 13664

Why do you have all those addins? You don't have Exchange so I'd not expect them to provide any benefit. If you haven't I'd try unchecking all of them. I know in the past I've removed all addins to get things working properly in a non-Exchange environment.

 

[carmen617]

Why do you have all those addins? You don't have Exchange so I'd not expect them to provide any benefit. If you haven't I'd try unchecking all of them. I know in the past I've removed all addins to get things working properly in a non-Exchange environment.

They are just included and on by default in Outlook, however you make a good point. I don't need them, and maybe they are causing issues, so I have disabled them all and will see if any improvement.

 

[britechguy]

@carmen617

Just curious if you've checked your polling interval? Very often connections are maintained, rather than dropped, once a certain frequency of polling is used.

The once every 30 minutes default is an eon between checks.

 

[YeOldeStonecat]

All well and good, but plenty of people do use it, and are comfortable with it, and want to use it -

Oh yes...I know, lots of people make mistakes or make a bad choice. I live and breath in Outlook, setup new accounts..quite a few...every single day, and support a few thousand installs of Outlook.
I'd rather drag my nuts through 58 miles of molten lava than support Outlook on a home grade email account though, been in this IT game for 30 years, seen it all, and more. I've learned where to draw my line in the sand.

All this troubleshooting here on this situation, including your time posting, and reading, this thread..are you billing for it?

 

[britechguy]

are you billing for it?

Do you pay the slightest bit of attention to what has been said during a thread? It appears not. See post #52

Answered a while back. Billing yourself really has no benefit. And for those of us who support residential clients almost exclusively, knowing the ins and outs of what happens to clients who might face the same situation is worth its weight in gold.

 

[YeOldeStonecat]

Do you pay the slightest bit of attention to what has been said during a thread? It appears not. See post #52

...and it's really not that big of a stretch....that trying to setup the same nightmare of "Outlook <==> ICrap" will lead to wasted time down the road if you think it's acceptable to setup and attempt to support the same disasterous scenarios for clients that pay for things getting setup/support. The old "practice what you preach" thing.

Learn what works....err...or not.... //shrug