Title: Entourage IMAP access to CommuniGate Pro
This question may be too specific to be answerable by anyone but the development team, but here goes...

I administer a CommuniGatePro 3.5.9 server and access my mail via IMAP with Entourage Version 10.1.1 (2418). Things are generally good except periodically at no regular interval that I can determine, Entourage throws up the following error:

Error
Mail could not be received at this time.
Explanation
Invalid account ID or password. Check your account settings.

Of course nothing has changed on either the server or in my account settings. The next connection to the server completes without error. If I check the server logs, this is the relevant information logged:

09:19:00.71 5 IMAP connection request from [192.168.105.97], socket=44
09:19:00.71 4 IMAP-01760([192.168.105.97]) got connection on [123.123.123.123], port 143
09:19:00.71 5 IMAP-01760([192.168.105.97]) out: * OK domain.com IMAP Server ready\r\n
09:19:00.72 5 IMAP-01760([192.168.105.97]) inp: A000 CAPABILITY
09:19:00.72 5 IMAP-01760([192.168.105.97]) out: * CAPABILITY IMAP4 IMAP4REV1 ACL NAMESPACE UIDPLUS IDLE LITERAL+ QUOTA ID MULTIAPPEND STARTTLS AUTH=LOGIN AUTH=PLAIN AUTH=CRAM-MD5 AUTH=DIGEST-MD5 AUTH=
09:19:00.92 5 IMAP-01760([192.168.105.97]) inp: A001 AUTHENTICATE NTLM
09:19:00.92 5 IMAP-01760([192.168.105.97]) NTLM SASL challenge: 76054009
09:19:00.92 5 IMAP-01760([192.168.105.97]) out: + \r\n
09:19:00.92 5 IMAP-01760([192.168.105.97]) inp: TlRMTVNTUAABAAAAB4IIIAAAAAAAAAAAAAAAAAAAAAA=
09:19:00.92 5 IMAP-01760([192.168.105.97]) NTLM SASL inp:  4E 54 4C 4D 53 53 50 00 01 00 00 00 07 82 08 20 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00
09:19:00.92 5 IMAP-01760([192.168.105.97]) NTLM SASL out:  4E 54 4C 4D 53 53 50 00 02 00 00 00 00 00 00 00 30 00 00 00 07 82 08 20 37 36 30 35 34 30 30 39 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00
09:19:00.92 5 IMAP-01760([192.168.105.97]) out: + TlRMTVNTUAACAAAAAAAAADAAAAAHggggNzYwNTQwMDkAAAAAAAAAAAAAAAAAAAAA\r\n
09:19:00.93 5 IMAP-01760([192.168.105.97]) inp: TlRMTVNTUAADAAAAGAAYAJAAAAAwADAAqAAAACQAJABAAAAACAAIAGQAAAAkACQAbAAAAAAAAAAAAADYBYIIIG0AYQBpAGwALgBkAGEAaQBsAGUAeQBhAGQAcwAuAGMAbwBtAHIAZQBtAG8AbQBhAGkA
09:19:00.93 5 IMAP-01760([192.168.105.97]) NTLM SASL inp:  4E 54 4C 4D 53 53 50 00 03 00 00 00 18 00 18 00 90 00 00 00 30 00 30 00 A8 00 00 00 24 00 24 00 40 00 00 00 08 00 08 00 64 00 00 00 24 00 24
09:19:00.93 5 IMAP-01760([192.168.105.97]) NTLM SASL name: [EMAIL PROTECTED]
09:19:00.93 5 IMAP-01760([192.168.105.97]) NTLM SASL password: INWTlWf2lAbv3TVfDztRL4Vxn1RLEtPhC5UEbKsDBeiPLuRKeEYytwEBAAAAAAAA
09:19:00.93 1 ACCOUNT(remo) incorrect password. Login attempt from [192.168.105.97]
09:19:02.93 5 IMAP-01760([192.168.105.97]) out: A001 NO incorrect password\r\n
09:19:02.94 5 IMAP-01760([192.168.105.97]) inp: A002 LOGIN "remo" "password"
09:19:02.94 2 IMAP-01760([192.168.105.97]) '[EMAIL PROTECTED]' connected from [192.168.105.97]
09:19:02.94 5 IMAP-01760([192.168.105.97]) out: A002 OK completed\r\n
09:19:03.12 5 IMAP-01760([192.168.105.97]) inp: A003 LIST "" ""
09:19:03.12 5 IMAP-01760([192.168.105.97]) out: * LIST () "/" ""\r\nA003 OK completed\r\n
09:19:03.14 5 IMAP-01760([192.168.105.97]) inp: A004 SELECT "Postmaster"
09:19:03.14 5 IMAP-01760([192.168.105.97]) out: * FLAGS (\Answered \Flagged \Deleted \Seen \Draft)\r\n* OK [PERMANENTFLAGS (\Answered \Flagged \Deleted \Seen \Draft)] limited\r\n* 0 EXISTS\r\n* 0 RECE
09:19:03.46 5 IMAP-01760([192.168.105.97]) inp: A005 LOGOUT
09:19:03.46 5 IMAP-01760([192.168.105.97]) out: * BYE domain.com IMAP Server closing connection\r\nA005 OK completed\r\n
09:19:03.46 2 IMAP-01760([192.168.105.97]) '[EMAIL PROTECTED]' disconnected ([192.168.105.97])
09:19:03.46 4 IMAP-01760([192.168.105.97]) closing connection
09:19:03.46 4 IMAP-01760([192.168.105.97]) releasing stream

My IMAP account is not configured to access the server securely:

This IMAP service requires a secure connection (SSL)  = unchecked
Override default IMAP port: 143  = unchecked
Always use secure password  = unchecked

It appears that when Entourage accesses a server advertising NTLM capability it defaults to trying that method first and if it doesn’t succeed drops back to clear-text authentication. But why is it generating an error sometimes? Either ignore the failure and drop back to clear-text or generate an error consistently every time, right?

Can anyone provide any insight into the matter?

-Remo Del Bello

--
"Even if a man chops off your hand with a sword, you still have two nice sharp bones to stick in his eyes."
- Kendo proverb

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