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Customers with iPhones unable to connect
Problem reported by AWRData - 10/30/2024 at 1:01 PM
Resolved
I am having intermittent problems with users on iPhones having trouble with both initial setup and on-going connections to my SmarterMail server.

I have had hands-on sessions with these customers during which I am unable to establish any connection to the server.  It is not an IP issue, so far as I can tell, as workstations behind the same IP address can connect.

This has now crept into two customers.  A small number of devices, but still a large inconvenience when these customers had no problems with their email previous to my service.

Has anyone run into issues with the iPhone Mail client suddenly stopping working, or even never being able to get connected in the first place?  Standard troubleshooting applied: restart, delete account and re-add, blah blah blah.  Hell, at one point i had them using Outlook just because it would connect!

I desperately need to get this fixed, or at least identify the failure point, not just for these customers, but as I am expected to take on a local ISP email accounts.
Jereming Chen Replied
10/30/2024 at 4:51 PM
Employee Post
Hello,

We have not seen this issue, but we would be more than happy to test this. Could you open a ticket with details and we will see what we can do in regards to troubleshooting your issue?
Jereming Chen
Internal Network/System Administrator
SmarterTools Inc.
Make sure that the Iphones are up to date firmware wise.

We have seen issues that they wont connect until a restart and update.
AWRData Replied
10/31/2024 at 10:11 AM
Please refer to the first post before answering.  As indicated, we have completed basic and standard troubleshooting steps.
Sorry for trying to help. Will escort myself out.
Tony Scholz Replied
10/31/2024 at 12:16 PM
Employee Post
Hello, 

I have been doing some testing locally on my iPhone on several different servers using the native email client and have not seen any issues. The best bet would be to open a ticket so that we can test against your server directly to see if we can replicate the issue or find any issues related to the setup. Apple prefers SSL connections over TLS connections and any type of certificate hiccup can cause issues. 
Tony Scholz
Lead Network/System Administrator
SmarterTools Inc.
D
Daniel Replied
11/4/2024 at 3:47 AM
Hello,


I had the same issue with 2 users in both cases i ended up changing the password (i gave all of our users a random generated 35 password) there seem to be a problem with some special characters on Iphones.

Maybe its the same problem for you..
Kyle Kerst Replied
11/4/2024 at 6:33 AM
Employee Post
Hi Daniel! Quick question for you on your scenario - did you identify any specific special characters that were problematic? If you could also provide some details on iPhone version, mail client, and the protocol used in those instances that should help us narrow things down.
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
D
Daniel Replied
11/4/2024 at 7:17 AM
Hello,
Well one of the problematic Passwords was this one : j8Wm-V-o(k3k9xQYeSAHApRuoQIs8)2iuGd

I have absolutly no idea of the Iphone version but it was the Outlook client (wish also bugs on androids sometimes).

So no sorry i cant help any more than this 
AWRData Replied
11/4/2024 at 7:47 AM
Aw, man.  I was immediately hopeful the password thing would be a simple solution.  Unfortunately, we are talking about the native iPhone mail client over IMAP.  I am trying to wrangle one of the affected users to do some focused troubleshooting this week.
D
Daniel Replied
11/4/2024 at 8:37 AM
Oh sorry (we are using eas)  dumb question but imap is enabled for that user ?
AWRData Replied
11/4/2024 at 9:06 AM
I just checked, and only one of the users are using special characters in their passwords, which is "$".
Kyle Kerst Replied
11/4/2024 at 9:47 AM
Employee Post
I wasn't able to replicate initial setup, sync, or subsequent send/receive issues with multiple $ in my password so I'm going to test some of the ones in thew other example above to see if I can narrow down what might be a problem there. In the meantime, I do know Outlook Mobile does some caching server-side and so if the password was recently changed it may be caching you're running into rather than an issue with that specific password. I'll do some more testing and I'm able to get it replicated I'll follow up here to let you all know.
Kyle Kerst
Lead Internal Network/System Administrator
SmarterTools Inc.
Adam Lewis Replied
11/6/2024 at 9:09 AM
We are having iPhone connection issues since the latest build was installed. They all seem to be related to one domain, but everything worked fine until Build 9056 now users are getting all types of connectivity issues. They seem to be related to the way we have SSL's working or something, but again, worked fine until the latest build. We were able to get them to all switched from the native iOS app to Outlook and use EAS and that's working. I don't have the time to debug the IMAP issue, but it's there.
John Quest Replied
11/6/2024 at 9:46 AM
I do not think this has anything to do with Smartermail. On my own iPhone, I have been seeing this problem intermittently using the built-in iPhone email client connecting to a Rackspace email server.  My Yahoo email client connecting to Yahoo email and the eM Client connecting to Rackspace email server have no such problem.

This for me started after I updated my iPhone about 10 days ago.
Andrew Barker Replied
11/7/2024 at 5:00 PM
Employee Post
We have occasional conversations with Apple. During one of those recent conversations, they mentioned that iOS 18 included revisions to their IMAP code. John's experience seems to indicate that this might be related to those changes.

If anyone experiencing this behavior would submit a report with Apple's Feedback Assistant, then send us the feedback ID in a support ticket, we can try asking someone at Apple about the issue.

Andrew Barker
Lead Software Developer
SmarterTools Inc.
www.smartertools.com 
AWRData Replied
11/7/2024 at 5:11 PM
This correlates with our problems: all affected customers are running iOS 18.  I spoke with several customers today using iPhones that are not on 18 and are working fine.
J
Jack. Replied
11/7/2024 at 6:54 PM
Marked As Resolution
The issue is related to iOS 18 with IMAP, it is not a problem with SmarterMail.






-------------------------------------------------
The suggested solution involves adding a forward slash (/) in the Path Prefix field under the Mail app’s account settings.
Here’s how to do it:
  1. Go to Settings > Apps > Mail > Mail Accounts > [Your IMAP Account] > Account Settings > Advanced.
  2. Locate the IMAP Path Prefix in the Incoming Settings section.
  3. If the field has a greyed-out /, retype the forward slash (/) so it turns white.
  4. Back out of the menu and press Done.
  5. Close the Settings and Mail apps, then reopen Mail to see if the issue is resolved.
-------------------------------------------------
We have seen this recently on macbooks not able to fetch attacthments on IMAP.
AWRData Replied
11/12/2024 at 9:57 PM
A customer reported that deleting the account from her iPhone mail app, re-adding it, then going into the settings to re-set the IMAP root to "/" worked for her.

The other customers are still pending.
D
Daniel Replied
12/16/2024 at 4:45 AM
Hello,

I am not able to add a mailbox on an iphone (EAS) the old passowrd was F/k\+!u!eqHEz$6Gqf#Sbq#F,
(had to add him 2 accounts the first one could be added whitot any problem (but has neither /\+!$# in it).

Since trying to add id does not event trigger ids i suppose that its the iphone that does not even gets to the point of trying it.

Iphone : 14
ios 16.3.1
AWRData Replied
12/16/2024 at 10:13 AM
I have been away for a few weeks, unable to work with day-to-day.  Reported to me that all customers affected were able to follow the procedure above to correct the issue: delete account, add account, re-set the root folder path to "/".
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