Outlook and IMAP

[britechguy]

...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

The problem is your assertion that, "it doesn't work," is in direct opposition to my entire professional experience, so far, which is not scant. That might give you just a bit of pause, or not.

The occasional thorny issue and "doesn't work" are far, far from the same thing.

 

[frase]

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?

Well said ol friend

 

[fincoder]

residential grade email POP/IMAP support was partially added to Outlook later, as an afterthought

Added 24 years ago with Outlook 98, only the second version (Outlook 97 was the first one). By that time scale it could hardly be called an afterthought.

 

[Sky-Knight]

That install looks clean, so now onto other things.

Have you tried different DNS servers? What DNS are you using? Are you using a filtering DNS service?

When it's broken, does nslookup mail server name here work?

 

[YeOldeStonecat]

Added 24 years ago with Outlook 98, only the second version (Outlook 97 was the first one). By that time scale it could hardly be called an afterthought.

Yes I deployed/supported many hundreds of Outlook installs back then, as well as Exchange servers, and I taught classes on using Outlook to companies that had Exchange installed.

"Outlook 97 is an ENTEPRISE GRADE email client. It is primarily intended for use with Microsoft Exchange Server"

Microsoft Outlook 97

Microsoft Outlook (not to be confused with Outlook Express) is an enterprise grade e-mail client. It is primarily intended for use with Microsoft Exchange Server. It was available as both a stand-alone product and as part of Microsoft Office.

winworldpc.com

Microsoft has the basic email clients ..starting with Outlook Express, and onwards, to be used with residential email (pop/imap)...and they work quite well. As well as the plethora of 3rd party email clients out there which work very well with pop/imap.

If you gather a lot of "experienced" IT people in a room and start talking about Outlook, and IMAP, you'll get a lot of moans and groans, if not a bunch of sarcasm asking why you want to do that. You'll never get 100% of a group of "experienced" IT people saying Outlook <==> IMAP is a good idea. Sure you can find some who have not run into problems, I guarantee they don't have a large client base to base from...that's why I say if you gather a room full of "experienced" IT people...

Yes, we know that you can connect Outlook with GMail or <insert your ISPs freebie email>, etc.
But...most of us also know that, over time, you'll have to battle with Outlook and it's connection to that mail system, due to some error. Google often makes subtle changes to their email system and its protocols...and that can break Outlook. Outlook also gets cranky with larger mailboxes if they're IMAP.

To me, if ones email setup requires frequent attention to troubleshoot...it is not a good choice of an email system.
To me, one should spent something like 30 seconds to configure an email account, and then it's rock solid from that point on. Someone should not have to keep calling some IT/computer person to keep troubleshooting every several months or every year or so.

Part of the job of an IT person it to guide the client into a good reliable choice for a system, "things that work well". I wouldn't feel right recommending a system to a client...knowing that system was not good.

 

[carmen617]

Well, I don't want to be premature, and I am probably about to jinx myself, but since turning off all the built in Outlook add-ins I haven't had an issue, and send/receive has been fast, smooth, and painless. If this is the solution it's great, as that's a nice easy fix I can roll out to any client having issues. If things continue smoothly for the next day or so, I might reenable them one by one to see if I can pinpoint the troublemaker.

As far as the debate about using Outlook for anything other than a Microsoft exchange account, well I am clearly, firmly, a believer in doing so. I have used Outlook as my main email client for 20 years, and never had major issues until recently. Nothing, absolutely nothing, in our world works perfectly every time. If it did, we wouldn't have a way to make money. I am perfectly content to tell my clients that Outlook will work "OK", and even give them the solution for times that it hangs. I just can't recommend a product that is hanging daily or worse, and it's my (our) job to try to track down what's causing the issues and find a solution.

Thanks for all the ideas and potential fixes, especially Mark for suggesting I disable the standard add-ins. Signing off now for a bit, will post again if anything changes.

 

[fincoder]

If you gather a lot of "experienced" IT people in a room and start talking about Outlook, and IMAP, you'll get a lot of moans and groans

Sure, because "experienced" means old means they've dealt with Outlook from the early days when it wasn't recommended for IMAP. I wouldn't recommend IMAP in Outlook 2007 or earlier. 2010 had some minor issues, but since then IMAP works well in Outlook, in my opinion far better than Outlook Express and Windows Live Mail.

"Outlook 97 is an ENTEPRISE GRADE email client. It is primarily intended for use with Microsoft Exchange Server"

Of course! But 20 years is a long time in IT, even Microsoft products have evolved somewhat

Yes, we know that you can connect Outlook with GMail or <insert your ISPs freebie email>, etc.
But...most of us also know that, over time, you'll have to battle with Outlook and it's connection to that mail system, due to some error. Google often makes subtle changes to their email system and its protocols...and that can break Outlook.

The main issue with Gmail in Outlook was lack of OAUTH2 support. It took way longer than it should have for Outlook to support that, but in recent years they have. So now Gmail works well in Outlook (except no contacts/calendar sync, those wanting that should consider emClient).

Outlook also gets cranky with larger mailboxes if they're IMAP.

I haven't seen that but I'll accept the point that IMAP support in Outlook could still be improved.

To me, one should spent something like 30 seconds to configure an email account, and then it's rock solid from that point on. Someone should not have to keep calling some IT/computer person to keep troubleshooting every several months or every year or so.

Gmail setup in Outlook is now very easy (and seems solid to me), thanks to OAUTH2 support added in recent years.

 

[Sky-Knight]

Yeah adding a gmail account to Outlook 2016/19/22 is identical in process to adding an Exchange mailbox.

Feed it the email address, process the OAuth prompt, watch it populate.

It's the calendar / contact sync that's the problem.

 

[YeOldeStonecat]

Sure, because "experienced" means old means they've dealt with Outlook from the early days when it wasn't recommended for IMAP. I wouldn't recommend IMAP in Outlook 2007 or earlier. 2010 had some minor issues, but since then IMAP works well in Outlook, in my opinion far better than Outlook Express and Windows Live Mail.

2013 also had issues with IMAP, I know, we had clients on it and when some update came out, the following week was all hell broken loose. Pretty sure was even threads on this forum about it.

I know some people will insist on using it, like selling 300 dollar computers to clients, not raising the bar for their clients, and there will be those that support residential clients thus are stuck with this. We're fortunate to only have 3-4 business clients using GMail, they're fairly new clients we've taken on with an understanding they'll get migrated to 365 in due time so we have the patience to wait...and 3 of 'em use Gmail like Google intended....via Chrome browser.

We're also an MSP, clients on fixed monthly payments....so we want things to run smooth. If things are not smooth, if we get calls to fix things that should be working smooth, the time we spent makes that client less profitable. Aka we eat that time. So I guess I can see why others don't mind...it's a billable.

 

[Sky-Knight]

So I guess I can see why others don't mind...it's a billable.

This... 1000 times this. We have countless shops out there that profit from perpetuating unsustainable solutions. And the also wonder why the reputation of our industry is so bad we can't even be trusted with our own google adwords!

 

[britechguy]

It is amazing to see how willing those with the, "You can't do IMAP and Outlook reliably," perspective are to ignore tech after tech after tech who are out and out stating, based on direct experience: "You can, and we do."

And it's not that we are "perpetuating unsustainable solutions." Our own professional experiences have shown us that in all the modern versions of Outlook (including 2010 and 2013, plus all later) that IMAP and Outlook get along just fine, thanks.

This is just the biggest example of willful blindness that I have ever witnessed on any forum dedicated to technical support.

If you want to argue about Google and Contacts/Calendars, that's a completely separate ball of wax. But even in that space once I've set up the third party tools, correctly, and with current OAUTH authentication they just keep running and running and running with zero care and feeding. And heaven knows, if they didn't, I'd never suggest to a single one of my blind or visually-impaired clientele that they use same.

Post-Script: As to whether it's billable or not, that's irrelevant to those of us who do care about our reputations and don't want to be constantly bothered with things breaking. But, boy, if this topic doesn't also point up that the MSP model is about cash flow without doing anything (and I understand that it is, and why it is) then nothing will.

 

[YeOldeStonecat]

What "tech after tech after tech"....do you speak of? I just scrolled back through all 4 pages. The "use something other than Outlook with IMAP" line is longer than the "We love Outlook with IMAP" line. Do a search in these forums of "Outlook IMAP" and boyyyyyy...does one find a lot of threads ...pages..and pages...and pages worth....of frustrated techs...and those who also claim "Avoid it" like I do.

Regardless, like Intel vs AMD, like ATI (AMD) vs nVidia, like Windows vs Mac, like Chrome vs Firefox, like Democrats vs Republicans...nobody is going to change the others mind.

And yes, MSP is about minimizing "stupid repair time that should have been avoided in the first place"..and instead spending time in pro-active duties...checking firewalls, checking backups, checking patch management, checking SEIM logs, after hours/before hours maintenance. And yes, I'm almost 60, I like my "cruising social media time"...I've earned it. And my opinion and aversion of Outlook <==> IMAP comes from 30 years and right now around 3,000 plus under under our watch. While yes the majority of those is on 365, we still get handfuls which use residential email for a period of time as we onboard them, or those who want to stay on it, perhaps stay "break/fix". So my exposure to IMAP is still quite wide.

I also see the heavier use side of things... because we cater to 99.99999% biz clients. So we see people who push their systems, 15, 20, 25, and more gig sized mailboxes.....and often a lot more. Heck mine is larger than 30, my wifes is probably 40. I see Outlook just get wonky with IMAP and mailboxes that big. We have plenty of people on 365 with over 50 and 75 gig mailboxes...purrs like a kitten! And people in business should absolutely be able to store mailboxes that large....this isn't the dial up days and POP email. This is modern times with fast broadband and high power computers, HUGE mailbox on proper biz grade email systems runs great...I have the numbers under our command to verify that. Yes, I'll admit I see it run OK with small simple setups, small mailboxes, true residential users with light use. Clunky to migrate data to a new computer (calendar, contacts...just not as smooth at it is with 365). Add to the mess, different ISPs have their own funky twist of IMAP. Comcraps mail servers aren't the same as GMails. Not sure if that's a good thing, or a bad thing. But anyways, like I said, nobody is changing anyone's mind here, so we'll have to go back to our corners, or find the exit door of this thread.

 

[fincoder]

IMAP in Outlook isn't perfect, but it works reasonably well. Other email client apps aren't really any better, except maybe emClient. Thunderbird is OK but it's UI is very dated and many people don't like it.

If so many residential users didn't already have Outlook in their 365 subscription, I'd be suggesting emClient more. But it's one license per computer, even the free version, so not so good for multi-computer households.

If I'm asked what kind of free email should be created, I always recommend outlook.com because it works well with Outlook and even works with Mail/People/Calendar. So many people have gmail and ISP email addresses though.

 

[Sky-Knight]

Only problem I run into with M365 mailboxes >50gb is the default to keep all mail on the endpoint and Outlook cratering when the OST hits 50gb.

Easily fixed of course, but still annoying.

 

[carmen617]

OK, I said I would circle back if anything was different, and of course I had jinxed myself and found my mailboxes unable to sync again shortly after I posted things were better. However, I now believe I have actually solved the problem, and also that it has little to do with IMAP and everything to do with Outlook. It occurred to me that I was having problems after I would go out - I would come back and Outlook would be disconnected and not reconnect. So I searched Outlook not reconnecting after sleep, and found plenty of other people having the same issue, IMAP or Exchange accounts all affected. So did a little looking at my own system, and changed MIMO Power Save Mode in my WiFi adapter from "Auto SMPS" to "No SMPS". It's been two days, the system has slept many times since then, and I haven't had a disconnect. So, I would call this thing solved, and it has no connection to IMAP at all.

 

[Markverhyden]

OK, I said I would circle back if anything was different, and of course I had jinxed myself and found my mailboxes unable to sync again shortly after I posted things were better. However, I now believe I have actually solved the problem, and also that it has little to do with IMAP and everything to do with Outlook. It occurred to me that I was having problems after I would go out - I would come back and Outlook would be disconnected and not reconnect. So I searched Outlook not reconnecting after sleep, and found plenty of other people having the same issue, IMAP or Exchange accounts all affected. So did a little looking at my own system, and changed MIMO Power Save Mode in my WiFi adapter from "Auto SMPS" to "No SMPS". It's been two days, the system has slept many times since then, and I haven't had a disconnect. So, I would call this thing solved, and it has no connect to IMAP at all.

That makes sense. Out of curiosity did you go back and re-enable all those Outlook plugins?

 

[carmen617]

That makes sense. Out of curiosity did you go back and re-enable all those Outlook plugins?

Nope, don't need them and so won't turn them on again. I plan to check and change network adapter power settings for any client I have complaining about Outlook connectivity issues, will see how well this rolls out (as everybody's adapter power options are different).

 

[Sky-Knight]

Nope, don't need them and so won't turn them on again. I plan to check and change network adapter power settings for any client I have complaining about Outlook connectivity issues, will see how well this rolls out (as everybody's adapter power options are different).

This explains a few things, because I run scripts that turn power saving features off for NIC and WNICs both, because they cause no end of intermittent connectivity headaches.