[Dovecot] Problems with Apple Mail: Enter Password for Account "..."

[Professa Dementia]

On 5/22/2013 7:44 AM, Frank Röhm wrote:
> Hello
> 
> I have on Ubuntu 12.04 a postfix 2.9.3-2 mailserver with dovecot 2.0.19
> 
> I get email from my pc (thunderbird), my smartphone (k9mail) and my
> MacBook (Apple Mail 4.6 - 1085 on Mac OS 10.6.8) all with IMAP and SSL.
> 
> All is working normally but sometimes I get an error message from my
> MacBook, which is irritating. It says this (more or less):
> 
> "Enter Password for Account
> "..."
> 
> The IMAP-Server "..." rejected the password
> for user "..."
> 
> Enter your password again or cancel.
> ...
> o Remember this password in my keychain"
> 
> The password was NOT wrong, but anyway, if reenter it, Apple Mail won't
> accept it, the message will come again and again.

This is one of my pet peeves about Apple Mail and to some extent,
outlook.  If *any* error occurs during the authentication phase, Apple
Mail, usually mistakenly, displays the error about bad login credentials.

These errors may include such things as network problems, DNS issues,
local mailstore errors or corruption, issues with the mail server not
related to authentication, such as file locks, etc.

Besides being annoying, and misleading, Apple Mail will invalidate your
saved password, requiring you to enter it again.  If you have chosen a
strong password, you may not remember it, which can be a real pain in
the tuchus.

First look in your logs (Finder > Applications/Utilities > Console) to
see if there are any errors.  Second, if you can and it does not create
a security problem for you, temporarily use a non-SSL connection for
mail and a network sniffer like Wireshark to watch the transaction.
Right click on a packet and select "Follow TCP Stream", which is
particularly useful to see the interaction and any errors that may occur
during the interaction between Mail and the server.

The above also applies to similar problems with outlook.  Wireshark also
runs on windows, although mail error logging is not quite as good on
windows.

Dem