O365 Disconnect issues driving me and my client insane.

thecomputerguy

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I have a legal client who I sold a computer to a few years ago. It's a decent computer i5, 8GB, 250GB SSD, Windows 7 Pro. The computer runs great, she rarely has issues, and she doesn't screw around on the computer at all - she's one of those people whose icons haven't even moved their position since I installed the computer.

She started having Outlook issues a few months ago and I just can't for the life of me figure out what the hell is going on. This is especially pressuring because one of the main point she hired me was because of all the email issues she had with her previous IT guy since he installed an on-prem exchange server for literally 1 mailbox.

I moved her to O365 and for years everything worked fine. All of the sudden a few months ago Outlook would either disconnect from the exchange server, or just sit there saying "This folder was last updated at x:xxpm" which would indicate that it hadn't been updated in some time.

Here are some key points and things I've tried...

- She has excellent internet (Fiber with something like 75down/25up).
- Her other computer which is older never has the disconnection issues (so blaming it on MS is out).
- Her phone will continue to receive mail (obviously) while her desktop doesn't (which is what tells her it's disconnected again).
- Sometimes I won't hear from her for a week or two then she'll have 3-4 days where she can barely work because she's constantly disconnected.
- All of the other Lawyers in the Office are on O365 (that I setup), and none of them have issues.
- Closing and re-opening Outlook will only sometimes fix the issue, usually a full reboot is required, which she sometimes has to do 4-6 times a day (which infuriates her).
- I repair installed & uninstalled and reinstalled Outlook 2013.
- Setup many, many, new outlook profiles.
- Moved the OST off the SSD and onto a 7200rpm drive, then moved back
- Upgraded to Outlook 2016
- Setup many, many, new outlook profiles.
- Rebooted her networking equipment (very simple, she's plugged right into the modem/router from Verizon).
- Disabled the off-site/onsite backup from running during business hours
- Her internet always works, and I have been able to login to her computer to see the issue myself but I can't track down what the problem is so I reboot it and it's fixed because she can't be down all day.
- Disabling cached exchange mode makes everything run way to slow (unacceptable) and I don't even know if that would help.

I'm out of ideas, short of giving up and reformatting her computer (which I would hope fixes the issue) for free since I've billed her way too many times thinking the issue was resolved, then set it all back up from scratch, for free again.

Please help. This issue has been going on for months and we're both losing our minds over this issue.
 
What AV is on the computer? Any 3rd party plugins installed in Outlook?

Kabuto + Emsisoft

Addins are:

Microsoft Exchange Addin
Microsoft Sharepoint Server Colleague Import Add-in
Microsoft VBA for Outlook Addin
Natspeak Outlook Addin
Skype Meeting Addin for MS Office 2016
Timeslips addin for Outlook
 
I've had issues with the law firm I support between Timeslips and AV, in this case it was Sophos. I assume the plugins and AV are the same on both of her machines? Have you tried disabling add-ins to see what happens?
 
I've had issues with the law firm I support between Timeslips and AV, in this case it was Sophos. I assume the plugins and AV are the same on both of her machines? Have you tried disabling add-ins to see what happens?

Her other computer is a near identical setup except it doesn't have Timeslips installed, and it probably doesn't have skype ... I'll try disabling both of those.
 
How many folders? I have a client who has loads of email folders and once you get near 500 MAPI can’t sync them properly and it causes loads of issues such as sync errors, calendar appointments disappearing etc

Also have you tried deleting the OST file and letting Outlook create a new one?
 
How many folders? I have a client who has loads of email folders and once you get near 500 MAPI can’t sync them properly and it causes loads of issues such as sync errors, calendar appointments disappearing etc

Also have you tried deleting the OST file and letting Outlook create a new one?

Yeah so I checked the properties for her Outlook Data File and went to folders and then counted all the folders manually. Just in her inbox she has upwards of 830 folders in folders, and subfolders of those folders. Basically a folder for every client she's ever had. He OST is only like 3GB in size because Outlook is only downloading 6 months worth of email. She has more folders in her deleted items.

She doesn't have any issues with data disappearing but only this disconnect issue.
 
Yeah so I checked the properties for her Outlook Data File and went to folders and then counted all the folders manually. Just in her inbox she has upwards of 830 folders. Basically a folder for every client she's ever had. He OST is only like 3GB in size because Outlook is only downloading 6 months worth of email. She has more folders in her deleted items.

She doesn't have any issues with data disappearing but only this disconnect issue.

100% the folder limit is your issue.

https://danielkharman.wordpress.com/2016/09/10/revisiting-outlook-maximum-folder-limitations/

https://social.technet.microsoft.co...office-365-folder-limit-reached?forum=outlook
 
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