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Apple Mail not working with SM accounts
Problem reported by YS Tech - 1/22/2023 at 5:08 AM
Not A Problem
Hi,
i'm having problems with Apple Mail on my mac closing just after it opens. I've tried many things but it only seems to crash when I add an account that's on my SM server. Gmail, hotmail, outlook, etc. all work fine and it never crashes.
Any idea what the issue could be or where to look for an error?
Thanks

16 Replies

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Kyle Kerst Replied
Employee Post
Do any other clients crash like this when you add the same accounts to them? I'm thinking you have some saved/cached profile data in there causing issues. There is a process for flushing that out I found outlined here for reference:


That will flush out ALL account data from Mac Mail I believe, just a heads up!
Kyle Kerst IT Coordinator SmarterTools Inc. www.smartertools.com
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YS Tech Replied
Other mail apps seem to work fine, just Apple Mail.
There isn't a cache folder I can see to clear, I'm on the latest OS and I can't find a ~Library/Mail folder to clear.

It seems strange that it's only the accounts that use the SM server that have an issue and I've tried adding different ones on the server to Mail. As soon as I add any account on the SM server Apple Mail crashes.
Thanks
Anthony
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Tim Uzzanti Replied
Employee Post
Thats extremely odd and we have never had an incompatibility with Mac Mail.  It's VERY popular to use Mac Mail with SmarterMail and I use it as my primary client.  What MacOS version are you using?
Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com
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YS Tech Replied
Mac OS = 13.1 (Ventura)
I have 8 email accounts running on Mailspring client that are served from my SM server along with another 3 non SM email accounts.
I can run any non SM account in Apple Mail, as soon as I add any one of those 8 email account it crashes as soon as it opens.
This has worked fine with SM for years, It's really weird but that's whats happening.
I can't find any Apple Mail cache files otherwise I would try clearing these. I've deleted the email accounts completely and tried adding them again with the same result.

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Tim Uzzanti Replied
Employee Post
I would contact support and we can help you out.  Very odd indeed.
Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com
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YS Tech Replied
By the way it isn't just on my machine, my wife has the same issue on her mac (older OS version).
Nobody else on the server has mentioned they have an issue as yet, but that doesn't mean they don't.
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Scarab Replied
YS Tech,

We have a substantial Apple iOS & MacOS user-base that is using SmarterMail (about 90% of our user-base is Apple products). We've seen a lot of strange & weird Apple issues over the years and it always comes down to corrupted settings in the Apple Mail app (we tend to get a lot more of them after every OS update as the Mail app settings routinely get changed during updates).

Corruption in email clients happens all the time, and no email client is immune, including Apple Mail. If you are using IMAP then the easiest resolution is to remove the account from the Mail app, close the Mail app completely, and relaunch it, after which you can re-add your IMAP account. When setting up your SmarterMail account in Apple Mail it is strongly recommended to set the Authentication Method to "Password" or "Plaintext" instead of using the default "MD5-CRAM". (This is an ongoing problem with Apple going on 20 years now if your password contains a symbol and every time that Apple fixes it they break it again a couple of months later in another update.)

More recent versions of Mac Mail have a built-in feature to fix common types of local mailbox corruption. If you select your SmarterMail mailbox and then choose ‘Mailbox’ from the main menu, you would then select 'Rebuild' from the drop-down menu. This will begin the process of rebuilding your mailbox. When you rebuild your mailbox, copies of your emails stored on your local machine are deleted and downloaded again from your mail server. This process will take a longer time if you have a large mailbox with a lot of messages.

Post-Script: The Mail app crashing immediately upon attempting to retrieve email from your SmarterMail account could also be due to a malformed message in your SmarterMail account that Mac Mail cannot handle or is triggering a Junk Mail action in Mac Mail. Try logging in to your webmail and manually removing any questionable emails or emails with attachments to see if that fixes the Mail app crashes. (I've seen this happen with 8-bit encoded PDF mime-types as Mail Mail seems to expect 7-bit encoded PDF mime-types.)
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YS Tech Replied
Thanks for the detailed response, I'm not sure if all apply to my situation, although I'll see if any of these work.

Problems:
1) Apple Mail crashes as soon as I open it (so I can't rebuild)
2) Apple Mail crashes on start as soon as I add any of my 8 SM email accounts to it.
3) Non-SM accounts do not cause a crash (I have 5 accounts running fine on there, hotmail, outlook, gmail and a few of other work emails on different non-SM servers)
4) This is the same with my wife's Mac with her accounts (she has 2 SM accounts)

Common factors:
1) Apple Mail
2) Smartermail server
3) My connection

From your suggestions to try:
1) I'll have a look at the passwords and try changing one so it doesn't have any characters in it. See if that makes a difference.
2) I'll check the authentication method is correct.
3) I might create an account with no emails in it to see if that works

Thanks
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YS Tech Replied
ok, I created a test email account on a domain that has an account that fails.
The new account works ok, I have been able to send and receive from this test account.

So this would point to either the number of emails in the account being a problem, the mailbox size, the content in the emails, the account cache (if that's stored somewhere even when the account is deleted?) or something else?

But they only fail in Apple Mail and only the SM email accounts (apart from the test one I set up), I've tried various other mail clients and they all work fine with these accounts.

Looking in the IMAP logs I have this recorded a few times:

[2023.01.25] 12:42:44.525 [myip][50031480] Failed to fetch data item 29126 in 'ENVELOPE' for myemailaddress in Spam-Hi.
[2023.01.25] System.Exception: angled address does not end.
[2023.01.25]    at MailService.GroupFileAccess.RFC2822Helper.GetAngledAddressEndIndex(String text, Int32 startIndex)
[2023.01.25]    at MailService.GroupFileAccess.RFC2822AddressLine.Parse()
[2023.01.25]    at MailService.Protocols.IMAP.ImapMessageWrapper.AddressWrap(String address)
[2023.01.25]    at MailService.Protocols.IMAP.ImapMessageWrapper.GetEnvelope(RFC2822Header header, String& partValue)
[2023.01.25]    at MailService.Protocols.IMAP.ImapMessageWrapper.GetPart(User user, String partItem)
[2023.01.25]    at MailService.TcpServerLib.IMAP.IMAPSession.FetchDataItems(List`1 idList, List`1 itemList, Nullable`1 changedSince, List`1& replyArr)
[2023.01.25] 12:42:44.541 [81.103.106.102][50031480] disconnected at 1/25/2023 12:42:44 PM

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YS Tech Replied
That was a premature statement, the test email account I set up does not work either.
So anything set up in my SmarterMail doesn't work with Mac Mail (in my instance).
This account has 3 emails in it that are all from me, nothing else.

So my current setup/findings:
SM Build 8251
Mac OS Ventura 13.4.1
Outlook email account - works
Gmail email account - works
iCloud email account - works
Hotmail email account - works
a Fasthosts hosted email account - work
another third-party email account - work
Any email account on my mail server  - fails, even new ones.
All email accounts work in 3 other email clients I've tried.

I will try upgrading SM to the latest version to see if that makes any difference. Hopefully, it won't cause any more issues!
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Tim Uzzanti Replied
Employee Post
There are no known issues with Mail on MacOS.  But, this sounds like something is corrupted in your Mail app database on MacOS.  Mail does not fully delete or clean when you remove accounts.  If you don't have a ticket with support, you should get one created and we can help you clean all the data from application support etc.  FYI, I'm using MacOS Sonoma BETA and it's running great as well.
Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com
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YS Tech Replied
Thanks Tim, I'll do some deep cleaning and see if that helps.
It's definitely Mac Mail as everything works fine on my IOS devices (iPad and phones), but only Mac Mail related to SM for some reason (same on my other Mac with my wife's account).
Strangely they both stopped working around the same time, within a few days. So something definitely changed somewhere.
Very weird.
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Employee Replied
Employee Post
Thanks for the update. I went ahead and created a support ticket for you so we can give this a direct review. 

Kind regards,
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Rudolf Lindinger Replied
I have the same Problem with an IMAP-Account. Every Client (Google Mail on android and Apple Mailclient on iphone) opens and closes immediately. I installed this mailbox on an emclient on windows. Then i saw the errors. The Clients cannot download some of the imap-folders (Error BAD SELECT Folder does not exist). Then i renamed this folders in webmail and synced the imap new. Then it works. Problems were with special chars (&, ä, ß) - but not in all folders. There are other folder with the same chars and there the sync works. This behaviour has come with one of the last updates.

But i am not able to replicate this. i made a new mailbox and made a lot of folders with this chars in it - this never happened on the newly created mailbox.

Last week i lost one customer to MS365. He said, that with every new version come other bugs and problems and he is not interested to beta test this software...

regards
Rudolf
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YS Tech Replied
I'm currently looking at the issue with SM, I'll let you know if we resolve.
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YS Tech Replied
Now that's interesting.
I've just added the mail account that failed as a POP account instead of an IMAP account and it's fine.
There must be an issue with IMAP and my Apple Mail.
Any ideas?

PS. Had to resort to using MS Outlook, which works fine with all accounts!

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