Known issues with Apple apps and clients

We frequently see our customers encounter certain issues when using Mac Mail on a computer or Apple Mail on a mobile device. In general, we see that Apple often has issues with syncing Internet accounts and passwords for the calendar and contact apps.

On this page, we'll cover some of the most commonly encountered known issues. If you're having other issues with an Apple client, feel free to contact our support team for assistance.

Messages are disappearing from Trash

If you've noticed that emails seem to be disappearing from your Trash folder, and you're certain that you do not have auto-purge set up for this folder, you may want to check your Apple client.

Apple clients have an Erase deleted messages feature on their folders. We have seen some cases where a customer is not aware that this feature has been enabled for their Trash folder. Steps to disable this feature will differ depending on your device, but it can generally be found by going to Settings for your Apple device and finding Mailbox Behaviors. If you need guidance, our support team can help you find the exact steps for your device.

Depending on how long ago your mail client deleted these emails, you may still be able to restore them using our Restore data feature. We keep backups of deleted email for one week. 

Repeatedly asked for password when syncing calendars and contacts

In the past, we have seen that Apple will randomly drop the domain portion of a username when attempting to connect. Because the username is incomplete, the logins fail and ask for your password.

In recent updates, we are seeing that Apple shows the password error locally, without any authentication failure from our end. 

You can check your Login Log for these connections by following these steps:

  1. Open the Settings → Privacy & Security screen.
  2. Go to the Logged in sessions heading and click Review.
  3. Click View all logins in the last 4 weeks.
  4. Select Show logins from other applications.
  5. Make sure Show failed logins is checked.

Review the Login Log for recent CalDAV (calendar) logins and/or recent CardDAV (contacts) logins. If the recent CalDAV/CardDAV logins from your Apple client appear to all be successful (with the green check), this indicates that Apple is not connected to our servers when the logins fail. This points towards some internal issue with Apple authentication for contacts/calendars.

Unfortunately, there isn't much we can do about this from our end. We believe ignoring the password prompts would just work and the sync should continue to happen until you get the next prompt.

If possible, it may help for you to file a bug report with Apple. You can include in the report that the password prompts shows up even if there is no failed authentication at the CalDAV/CardDAV server, which clearly indicates a bug at the client side.

Keychain mixes up passwords

We've seen that the Keychain on a Mac mixes up saved passwords for different email accounts. Setting Mac Mail up with a new app password will at least temporarily resolve the issue, but it may occur again.

To prevent this issue from re-occurring, we suggest manually removing your Fastmail password from your Keychain by following these steps:

  1. Open the Keychain: click Finder > Go > Utilities > Keychain Access.
  2. In Keychain Access, select the Passwords category on the left to review the list of sites and services for which you've saved a password.
  3. Search for "Fastmail" in the next screen.
  4. Select all the passwords that you would like to delete/reset, right click and then choose Delete.

iOS Contacts adds new contacts to shared groups

We have seen that iOS Contacts will randomly choose to add new contacts to a shared contact group. Previously, a workaround for this issue was disabling the Fastmail account's on the iOS device. However, this no longer is possible after Apple's recent iOS updates.

To prevent this issue from re-occurring, you can force the device to only show non-shared contacts. To do so, you will need to remove and manually set up your Fastmail account contacts on your device, with the username set to the format username+Default@domain.tld. As an example, if your username is, you would want to enter your username as

Once this has been done, only the default address book (which is the non-shared group) will be synced. Unfortunately, this means you wouldn't be able to view shared contacts, if there are any.

Was this article helpful?
1 out of 15 found this helpful