Level 1

18 points

High Sierra and MS Exchange Problems anyone?

After 2 days the Apple mail app under High Sierra stopped working with Microsoft Exchange. New emails are not displayed. After removing the Exchange account, and setting up again, still no folders or mails can be received. The account (under email--->settings) definitely has connection to the exchange server (btw: Exchange 2010 on SBS), there's the "green" light. When setting up the new exchange account I noticed that this is handled differently to former versions of MacOS. There's no possibility to enter a "server", although in mail-settings-accounts the "internal and external URL" can be configured...but this changes nothing. Also (when having no server certificate) in former versions there was the small "warning triangle" beside the exchange account in the "tree" which could be clicked and the missing certificate could be ignored. Not so in High Sierra. Anyone with similar problems? Solution? thx

Posted on Sep 29, 2017 1:08 PM

Top-ranking reply

dianeoforegon

Level 5

7,305 points

Posted on Dec 5, 2017 5:23 PM

Let's clear up some confusion. I think I misunderstood when you wrote the following.

Exchange mail from Outlook in my Apple mail

You are not using Outlook.app but Mail.app to connect to your Exchange account. Both apps can connect to multiple types of email accounts. Exchange, IMAP and POP. What the window users in your company use to get Exchange has nothing to what you use on your Mac. What matters is the version of Exchange server.

Apple Mail can connect to Exchange as long as it meets one of these requirements.

Exchange Support

Requires Microsoft Office 365, Exchange 2016, Exchange 2013, or Exchange Server 2010 (SP2 or higher).

Try this to fix your Exchange account.

Remove the Exchange account in Mail > Preferences > Accounts.

This takes you to System Preferences > Internet Accounts.

Uncheck to remove the account. Not just uncheck Mail for Exchange.

In your User's Library/Mail folder....

Verify the Exchange data was removed when you removed the account.
Go to your User's Library > Mail > V5
You'll see alphanumeric folders, look inside. If you see the Outbox, this is the local "On My Mac" folders.
We don't want to find a folder for Exchange. Check to verify that is was removed. If you find the folder, then with Mail quit, delete the alphanumeric folder containing your Exchange data.
Clutter is a default Exchange folder, Exchange also has it's own Outbox. This shows Exchange account (the alphanumeric numbers are unique). You might also see custom folders you have created.

Next.... in V5 you should see a MailData folder. Delete any files with Envelope in the name.

Back in System Preferences > Internet Accounts

Add your Exchange account back.
Open Mail, It will reindex your messages.
Exchange will download again from the server.

My advice: When a new version of macOS is released DO NOT upgrade until it has matured. Unless there is some urgent need to upgrade then wait until the final version (.5 or .6) is released to upgrade. Lastly, check here in Apple Discussions to see if Exchange users are having any issues.

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58 replies

Oct 1, 2017 1:26 PM in response to PianoMax

I'm still searching for more answers on Exchange 2010 and Mail, but it seems that you would be better off with Sierra with Exchange 2010 SP1.

Trying to use old server software that is not fully updated is asking for problems with new versions of macOS. Newer versions of software work best with newer versions of Exchange ( Exchange 2013 and Exchange 2016)

Nov 12, 2017 9:01 AM in response to PianoMax

I fixed this by starting a VPN session into my workplace, and then starting Outlook. The connection and folder sync happened properly.

I stopped Outlook, then signed off the VPN. After that, Outlook works okay; connects and syncs no problem using regular internet connection. This also stopped Word from hanging on exiting.

So I guess it gets the certificate over VPN and can then use it in all instances.

Hope this helps!

tbeeze

Level 1

4 points

Dec 5, 2017 3:40 PM in response to PianoMax

Im still not receiving Exchange mail from Outlook in my Apple mail after upgrading to High Sierra. I have to select the particular mailbox and Rebuild it each time I want to receive new mail. So irritated that I keep falling for the upgrades that only cause more problems.

Nxt67

Level 1

4 points

Feb 19, 2018 7:33 AM in response to PianoMax

Just to add to this - the problem I had was on a Office 365 account with MFA enabled. I discovered that with MFA enabled the Microsoft Outlook App would work correctly with the proper MFA 2 factor authentication. However the inbuilt apps (calendar contacts etc) would not connect using a App password created from 365.

The solution was to change the Microsoft Outlook App to also use a App password rather than using the correct 2 factor method. Suddenly all the Apple apps authenticate correctly.

I'm presuming this is down to the account in the keychain being used for both applications? At least that's the only explanation i can come up with!

Oct 11, 2017 10:03 AM in response to PianoMax

Is your Exchange 2010 server running SP2?

Nov 28, 2017 1:32 AM in response to PianoMax

Same here - using Spark works proper with our EXCHANGE 2010 native without SPs!

Oct 1, 2017 11:35 AM in response to PianoMax

Did you select to Trust the certificate?

I'm assuming you have Outlook. Try adding to Outlook and see if it works.

tom_22

Level 1

15 points

Oct 11, 2017 1:13 AM in response to len.iphone

What is your Exchange build number/version?

leventv

Level 1

9 points

Oct 24, 2017 6:59 AM in response to mricect

I have the same problem. Just like you only rebuilding the mailbox fetches the new mail to inbox.

mlgiarra

Level 1

8 points

Feb 6, 2018 6:26 PM in response to dianeoforegon

Can you please say what one should do if the New User test works? I got mail downloads from Exchange server when I logged in as guest. What would the problem be in my "User's folder"?

PianoMax Author

Level 1

18 points

Oct 1, 2017 11:52 AM in response to dianeoforegon

The "trust" windows looked differently...before there was a checkbox to trust, which is now missing, instead there adre dropdown menus, which are by default "accept". So I let the default values. Outlook for Mac 2016 doesn't work with Exchange 2010 SP 1 so I cannot try this.

EDIT: With AIRMAIL3 the connection to Exchange 2010 SP1 works perfectly and all folders and mails are synced properly.

PianoMax Author

Level 1

18 points

Oct 1, 2017 12:26 PM in response to dianeoforegon

in my configuration the "Always trust" is pre-checked and I confirmed this with my password.

Outlook didn't work with Exchange 2010 SP 1 for ca. 2 years, whereas the Yosemite, El Capitan and Sierra Apple mail apps did without a problem.

I found no information about High Sierra ditching Exchange 2010 SP1 support, perhaps/probably Apple did, but at least they should inform about it.

Oct 2, 2017 6:25 AM in response to PianoMax

It should be noted that even as far as Microsoft themselves are concerned Exchange 2010 is end-of-life.

See https://support.microsoft.com/en-us/lifecycle/search?sort=PN&alpha=exchange%20se rver%202010&Filter=FilterNO&wa=wsignin1.0

If Microsoft consider it obsolete I see no reason why Apple should be expected to continue to support it.

Dec 5, 2017 3:47 PM in response to tbeeze

What version of Outlook? Outlook 2011 v14.7.7 is the last version of Outlook 2011. It's an End of Life product now. It's also 32-bit. 32-bit apps do not work well with High Sierra. You need to upgrade to Office 2016. You want the subscription not the product. Office 2018 is already in beta. subscription includes updates where a retail copy does not even qualify for upgrade pricing.

If you want to do the 30 day trial download here.

http://products.office.com/en-us/try

Buy via Amazon and get a keycard for approx $85 for the first year for 5 installs but if you have only one device it's ~$59.00. Microsoft charges more per year.

tbeeze

Level 1

4 points

Dec 5, 2017 4:10 PM in response to dianeoforegon

Thanks. I work remotely for a company that uses the 2010 version of Outlook. I'm the only Mac and trying to explain the issue gets me the "why did you upgrade without telling us?" which doesn't matter because they wouldn't have known to begin with. So, explaining that the company needs to upgrade their Outlook for my one little Mac won't get me anywhere. I'll be better off uninstalling High Sierra and going back to what I had before. I can also access my Outlook mail via Safari (which most in the company access via a browser) so I may just remove it from Apple Mail. It also comes to my phone just fine and I am using the latest iOS on that. By the way there's no Microsoft product in my Applications folder so I am thinking it's just logging in to their server that downloads my company email. ??

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High Sierra and MS Exchange Problems anyone?