Cannot Send Mail An error occurred while delivering this message

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Level 1

15 points

Cannot Send Mail An error occurred while delivering this message

Company Email intermittently gets this error when sending emails, but the email sends to intendent recipients. Problem happens on Wifi or Cellular with a good connection.

Trouble Shooting Steps:

I've re-setup the Email multiple times.

I've updated the iPhone 13 IOS from 15.* to 16.2

I've tested this on 2 different devices:

iPhone 13 Pro Max IOS 16.2

iPhone 14 Pro Max IOS 16.2

Ran Maintenance on User's email file

Opened a ticket with HCL Traveler Support, they indicate this is an Apple Device Problem.

This happens on Wifi or Cellular

iPhone 14 Pro Max

Posted on Jan 4, 2023 10:20 AM

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Answer 1

Top-ranking reply

Adam509

Level 1

8 points

Jan 5, 2023 9:44 AM in response to Marsorarksz

I'm having the EXACT same issue with a particular user exactly as you described! "Cannot Send Mail" but message is still delivered. Doesn't seem to be any rhyme or reason for when it happens or which recipient they are sending to and when I try to send test messages to my own e-mail to replicate the problem they all go through without issue until he tries it later that night. Happens on both iPhone 14 and iPad fully updated to 16.2. Only other thing I changed recently before this started happening was adding deleted items to the "Push" list so they are always in sync. This user has a very large mailbox and mail sync set to "No Limit". I'm going to try removing deleted items from push, mail days to sync back to 1 Month and reset the mail account.

No issues with sending from Outlook on desktop or OWA so it does seem to be just on the Apple devices.

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Answer 2

Marsorarksz Author

Level 1

15 points

Jan 5, 2023 11:29 AM in response to Adam509

This user is only Syncing 1 month of email on his iPhone and iPad. I have not be able to reproduce the problem on the iPad.

I worked with Apple Tier 2 support and they had me remove and re-add the email. They also had me reset the Network Settings. Which did not fix the problem.

This problem happens inconsistent, but it happens more frequently when first opening the Mail then immediately forwarding an email.

We are using HCL Mail which uses HCL Traveler to sync mail to mobile devices.

This was Found in the Logs by HCL Traveler Support:

"As per checking on the logs, the device keeps sending a policy key 0 instead of the previously negotiated. Not only during a SendMail, but for pushAS D->S (a Push from the Device to the Server) so a new key needs to be sent and redo the requests.

[12/20 18:10:34.126] FINEST WD-7f71ed3a3700 USER NAME[835J2Q3PCT09T4NVV8D63R7VEO] WorkManager$WorkerRunnable.run#4272 Device sent a policy key of 0 which is zero or does not match the server stored policy key of 817277860, so a 449 HTTP return code would be sent except that the device has the known bug of not sending the policy key on the Settings request when done close to a Provision request. Therefore, we will allow this request and NOT return the 449.

So, while the device has sent the 449 for this request, Traveler ignores it due the the known bug.

A policy key 0 is sent for the sync request (1220-1810-32807_Sync_4_1862_in.xml) "Device sent a policy key of 0 which is zero or does not match the server stored policy key of 817277860, so a 449 HTTP return code should be sent." so the Sync out shows the 449 and a Provision is needed to reestablish the a policy key. After that the Sync is successful.

Cannot Send Mail An error occurred while delivering this message

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