Note: This guide is intended for TBA Berlin customers whose email inboxes are hosted by our hosting partner, Mittwald. If your inbox is with another provider, the server addresses and ports may differ.
Apple Mail: Constant password request when sending
Apple Mail sometimes suddenly asks for the password, even though sending previously worked. Even after entering it correctly, sending fails.
The cause is usually not the password itself, but outdated access data in the macOS keychain. Apple Mail accesses an old entry that the server rejects.
Solution: Clean up Apple “Keychain”
- Quit Apple Mail – really quit (menu “Mail” → “Quit Mail”), don’t just close the window.
- Open Keychain Access – Open Spotlight Search (magnifying glass icon 🔍 in the menu bar at the top right), type
Schlüsselbundand open “Keychain Access.”
- Find and delete old entries – see instructions below.
- Restart Apple Mail – The next time you send or receive, a password prompt will appear. Enter your password and check “Save to Keychain”.
This will create a clean entry, and the password prompt should no longer appear.
How to find and delete the correct entries
In the Keychain Access, you will see a long list of saved passwords. Use the search field in the upper right corner and search for agenturserver.
You will then find entries with the following names:
com.apple.account.IMAP.password– for receivingcom.apple.account.SMTP.password– for sending
If only sending is not working: Delete only the SMTP entries.
If both receiving and sending are affected: Delete both the IMAP and SMTP entries.
Important: If you have multiple mailboxes with us, double-click an entry to check which account it belongs to before deleting it.
Tip: If you are unsure, you can move an entry to the trash instead of permanently deleting it first. If something doesn’t work afterwards, it can be restored.
Good to know: If you use Time Machine (recommended!), you can also restore earlier versions of the keychain from the backup in case of problems.
Not working? - More options
Please review the settings again first
If the problem persists, please check the sending settings: Mail → Preferences → Accounts → [Your Account] → Server Settings
- Hostname:
mail.agenturserver.de - Username: Your full email address
- Password: type it in instead of copying and pasting
- Port:
465* - Use SSL: enabled ✓
- Prefix must be
INBOX.
*Tip: If “Automatically manage connection settings” is enabled, Apple Mail may use incorrect values. Disable this option and manually enter the port.
You can find the complete settings for receiving and sending on our Configure email inbox page.
If cleaning is not sufficient
If the problem persists after deleting the agenturserver entries, old entries from the previous email provider may still be causing interference. Also search the keychain for:
sslinandsslout– old DomainFactory serversispgateway– also DomainFactory
Delete all entries that belong to the affected mailbox.
Additionally: In Apple Mail, check under Mail → Preferences → Accounts → [Your Account] → Server Settings to see if any old servers are still stored under “Outgoing Mail Server (SMTP)”. Remove any SMTP server entries that are no longer needed.
Workaround for a rare issue affecting users with multiple Apple devices
If you use iCloud Keychain, passwords are synchronized between all your Apple devices (Mac, iPhone, iPad). In rare cases, this can cause a deleted entry to be re-synchronized from another device, and the problem will occur again.
Recommendation: Temporarily disable iCloud Keychain before performing the cleanup:
- System Preferences → Apple ID → iCloud → Disable “Passwords & Keychain”
- Clean up the keychain (as described above)
- Start Apple Mail and re-enter the password
- Reactivate iCloud Keychain
The new, correct entry will then be transferred to all your devices.
If it still doesn’t work
If the password request continues to loop, a radical solution is often to remove* and re-add the mail account in Apple Mail (after the keychain has been cleaned).
*Important for POP3: When deleting a POP3 account, locally stored emails are lost. Deleting and setting up again should only be done with new mailboxes, not with mailboxes that are already in use. IMAP accounts are not affected because the emails remain on the server.
