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Sending mails via Mailmate result in a 550

#1928

Hi there,

i switched to a new MailServer where i added a postscreen filter with some dnsbl sites. Sadly (or luckily) one of them is blocking my ISPs IP Block and my Server is returning a 550 when i want to send a Mail:

20:05:15 Ready to run action (retry count: 0)
20:05:15 Clearing connection to mail.mydomain.de
20:05:15 Trying to connect to mail.mydomain.de on port 25 (CFNetwork) with STARTTLS (not required)
20:05:15 Resolved hostname (mail.mydomain.de).
20:05:15 Successful connection.
20:05:15 S: 220-mail.mydomain.de ESMTP Postfix
20:05:18 S: 220 mail.mydomain.de ESMTP Postfix
20:05:18 C: EHLO [10.86.11.34] // this is my local IP
20:05:18 S: 250-mail.mydomain.de
20:05:18 S: 250-SIZE 26214400
20:05:18 S: 250-ETRN
20:05:18 S: 250-STARTTLS
20:05:18 S: 250-ENHANCEDSTATUSCODES
20:05:18 S: 250-8BITMIME
20:05:18 S: 250 DSN
20:05:18 C: MAIL FROM:<thomas@mydomain.de> SIZE=5725
20:05:18 S: 250 2.1.0 Ok
20:05:18 C: RCPT TO:<thomas@receiverdomain.com>
20:05:18 S: 550 5.7.1 Service unavailable; client [1.1.1.1] blocked using zen.spamhaus.org . // 1.1.1.1 is my public ip
20:05:18 Error: Unexpected return code 550 (expected 250):
“5.7.1 Service unavailable; client [1.1.1.1] blocked using zen.spamhaus.org”. // 1.1.1.1 is my public ip
20:05:18 Error: The following recipients were rejected by the SMTP server:
    thomas@receiverdomain.com
Unexpected return code 550 (expected 250):
“5.7.1 Service unavailable; client [1.1.1.1] blocked using zen.spamhaus.org”. // 1.1.1.1 is my public ip
20:05:18 Error code: 1
20:05:18 Failed action (0). Reset observed read/write timeouts: 8/8

20:05:19 Handling reply
20:05:50 Sending request (521)
20:05:50 Handling request
20:05:50 C: QUIT
20:05:50 S: 221 2.0.0 Bye
20:05:50 Clearing connection to mail.mydomain.de
20:05:50 Ready to run action (retry count: 0)
20:05:50 Clearing connection to mail.mydomain.de
20:05:50 Completed action (3). Observed read/write timeouts: 8/8

When i want to send a mail via Thunderbird, everything works.
Whats the difference - how i could configure Mailmate to get it work?

I could provide you a example Mail-Account to debug/resolve this.

Thanks & Cheers,
Thomas

Reported by Thomas Helmrich · January 21st, 2018 @ 07:56 AM

State: new
Milestone: none
Assigned to: benny benny

Activity

  1. Thomas Helmrich
    Thomas Helmrich

    Need further informations?
    Can´t use Mailmate to send Mails at the moment.

    January 29th, 2018 @ 04:35 PM

  2. benny
    benny

    Sorry about the late response.

    It seems to me that Thunderbird must be connecting differently or at least with a different sending/recipient address. The message is rejected by the server because a client IP being blocked because of spam activity (according to the error message).

    Make sure that Thunderbird also connects on mail.mydomain.de (whatever the real hostname is) on port 25. You can hardcode MailMate to use a specific port if needed.

    If that doesn't work then you are welcome to provide a test account. You can use “Help ▸ Send Feedback” to see an email address which can be used to send me the needed info.

    January 29th, 2018 @ 07:09 PM

  3. Thomas Helmrich
    Thomas Helmrich

    Hi Benny,

    i will try to get the connection protocol from Thunderbird.
    BTW: Mail (MacOS) works too.

    I will provide you with a test account, but i have to set your IP to the blocklist of the postscreen filter, that you have the same env as me.

    Thanks & BG
    Thomas

    January 30th, 2018 @ 11:14 AM

  4. Thomas Helmrich
    Thomas Helmrich

    Thats my Thunderbird Log:

    -1502211136[10031c6b0]: SMTP Connecting to: mail.mydomain.de
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 220 mail.mydomain.de ESMTP Postfix
-1502211136[10031c6b0]: SMTP entering state: 14
-1502211136[10031c6b0]: SMTP Send: EHLO develth-macbook.develth.Home
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-mail.mydomain.de
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-PIPELINING
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-SIZE 26214400
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-ETRN
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-AUTH PLAIN LOGIN
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-AUTH=PLAIN LOGIN
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-ENHANCEDSTATUSCODES
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250-8BITMIME
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250 DSN
-1502211136[10031c6b0]: SMTP entering state: 4
-1502211136[10031c6b0]: SMTP entering state: 21
-1502211136[10031c6b0]: SMTP auth: server caps 0x20334, pref 0x300, failed 0x0, avail caps 0x300
-1502211136[10031c6b0]: (GSSAPI = 0x800, CRAM = 0x2000, NTLM = 0x4000, MSN =  0x8000, PLAIN = 0x200, LOGIN = 0x100, EXTERNAL = 0x400)
-1502211136[10031c6b0]: trying auth method 0x200
-1502211136[10031c6b0]: SMTP entering state: 16
-1502211136[10031c6b0]: SMTP AuthLoginStep1() for thomas@mydomain.de@¯˝

-1502211136[10031c6b0]: PLAIN auth
-1502211136[10031c6b0]: Logging suppressed for this command (it probably contained authentication information)
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 235 2.7.0 Authentication successful
-1502211136[10031c6b0]: SMTP entering state: 18
-1502211136[10031c6b0]: SMTP Login response, code 235
-1502211136[10031c6b0]: SMTP entering state: 3
-1502211136[10031c6b0]: SMTP Send: MAIL FROM:<thomas@mydomain.de> BODY=8BITMIME SIZE=445
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250 2.1.0 Ok
-1502211136[10031c6b0]: SMTP entering state: 5
-1502211136[10031c6b0]: SMTP Send: RCPT TO:<thomas@mytestdomain.com>
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250 2.1.5 Ok
-1502211136[10031c6b0]: SMTP entering state: 6
-1502211136[10031c6b0]: SMTP Send: DATA
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 354 End data with <CR><LF>.<CR><LF>
-1502211136[10031c6b0]: SMTP entering state: 7
-1502211136[10031c6b0]: SMTP entering state: 8
-1502211136[10031c6b0]: SMTP Send: .
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 250 2.0.0 Ok: queued as 70EBF68201A7
-1502211136[10031c6b0]: SMTP entering state: 9
-1502211136[10031c6b0]: SMTP Send: QUIT
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP entering state: 0
-1502211136[10031c6b0]: SMTP Response: 221 2.0.0 Bye
-1502211136[10031c6b0]: SMTP entering state: 10
-1502211136[10031c6b0]: SMTP entering state: 12
-1502211136[10031c6b0]: SMTP connection error quitting 804b0002, ignoring

    January 30th, 2018 @ 11:46 AM

  5. benny
    benny

    I don't see many differences and you might also be changing some values before posting here:

    20:05:18 C: RCPT TO:<thomas@receiverdomain.com>

    vs

    -1502211136[10031c6b0]: SMTP Send: RCPT TO:<thomas@mytestdomain.com>

    Make sure you use the exact same from/to addresses.

    Also try port 587 in MailMate and try with/without SSL enabled in the SMTP settings.

    (I really cannot see how MailMate plays a role here. If it does then we must look for something that triggers the server to reply differently when MailMate is connected versus when Thunderbird is connected.)

    January 30th, 2018 @ 12:26 PM

  6. Thomas Helmrich
    Thomas Helmrich

    The RCPT TO was the same in, i just edited it wrong.

    I see a big difference:
    Thunderbird first login, then sets RCPT TO and FROM.

    January 30th, 2018 @ 12:31 PM

  7. benny
    benny

    Ah, yes. I missed that. Do you have a username configured for the SMTP settings in the accounts editor?

    January 30th, 2018 @ 12:32 PM

  8. Thomas Helmrich
    Thomas Helmrich

    Also try port 587 in MailMate and try with/without SSL enabled in the SMTP settings.

    587 Works!

    Thanks.

    January 30th, 2018 @ 12:33 PM

  9. Thomas Helmrich
    Thomas Helmrich

    Ah, yes. I missed that. Do you have a username configured for the SMTP settings in the accounts editor?

    Yes, was all configured.
    I also tried SSL on / off - but never manual port set.

    Port 587 worked.

    January 30th, 2018 @ 12:34 PM

  10. benny
    benny

    I'm glad it works.

    It appears to indicate that MailMate skips authentication when using port 25, but it makes no sense to me why that would happen. Could you try to confirm this, e.g., by generating logs while both trying to send using port 25 and port 587 (all other settings being the same).

    January 30th, 2018 @ 12:37 PM

  11. Thomas Helmrich
    Thomas Helmrich

    I just checked Mailmate SMTP Log, with manual port set Mailmate first does the login, like Thunderbird.

    PORT Set; SSL ON = OK

    12:35:16 Sending request (1395)
12:35:16 Handling request
12:35:16 Ready to run action (retry count: 0)
12:35:16 Clearing connection to mail.mydomain.de
12:35:16 Trying to connect to mail.mydomain.de on port 587 (CFNetwork) with STARTTLS (required)
12:35:16 Resolved hostname (mail.mydomain.de).
12:35:16 Successful connection.
12:35:16 Ready for reading.
12:35:16 S: 220 mail.mydomain.de ESMTP Postfix
12:35:16 C: EHLO mydomain.de
12:35:16 S: 250-mail.mydomain.de
12:35:16 S: 250-PIPELINING
12:35:16 S: 250-SIZE 26214400
12:35:16 S: 250-ETRN
12:35:16 S: 250-STARTTLS
12:35:16 S: 250-ENHANCEDSTATUSCODES
12:35:16 S: 250-8BITMIME
12:35:16 S: 250 DSN
12:35:16 C: STARTTLS
12:35:16 S: 220 2.0.0 Ready to start TLS
12:35:16 Initiating secure connection...
12:35:16 Prepare secure connection...
12:35:16  Returned (4)...
12:35:16 Protocol version: kTLSProtocol12
12:35:16 C: EHLO mydomain.de
12:35:16 S: 250-mail.mydomain.de
12:35:16 S: 250-PIPELINING
12:35:16 S: 250-SIZE 26214400
12:35:16 S: 250-ETRN
12:35:16 S: 250-AUTH PLAIN LOGIN
12:35:16 S: 250-AUTH=PLAIN LOGIN
12:35:16 S: 250-ENHANCEDSTATUSCODES
12:35:16 S: 250-8BITMIME
12:35:16 S: 250 DSN
12:35:16 Retrieving password (keychain or user request)
12:35:16 C: AUTH PLAIN ••••••••••
12:35:16 S: 235 2.7.0 Authentication successful
12:35:16 C: MAIL FROM:<thomas@mydomain.de> SIZE=7610
12:35:17 S: 250 2.1.0 Ok
12:35:17 C: RCPT TO:<thomas@receiverdomain.com>
12:35:17 S: 250 2.1.5 Ok
12:35:17 C: DATA
12:35:17 S: 354 End data with <CR><LF>.<CR><LF>
12:35:17 C: From: "Thomas Helmrich" <thomas@mydomain.de>
12:35:17 C: To: "Thomas Helmrich" <thomas@receiverdomain.co ...
12:35:17    <7611 bytes> 
12:35:17 C: ... y3FvEvgZ5aNzs7ntMAAAAA
12:35:17 C: AAA=
12:35:17 C: --=_MailMate_4869358C-3F5D-416C-BD92-CEEDB2C4FF21_=--
12:35:17 C: .
12:35:17 S: 250 2.0.0 Ok: queued as 0C64168201A7
12:35:17 Completed action (0). Observed read/write timeouts: 8/8

12:35:17 Handling reply
12:35:47 Sending request (1399)
12:35:47 Handling request
12:35:47 Ready to run action (retry count: 0)
12:35:47 C: QUIT
12:35:47 S: 221 2.0.0 Bye
12:35:47 Clearing connection to mail.mydomain.de
12:35:47 Completed action (3). Observed read/write timeouts: 8/8

12:35:47 Handling reply

    January 30th, 2018 @ 12:37 PM

  12. benny
    benny

    Ah, I see why. When connecting to port 25 then the server tells MailMate it has no authentication methods available.

    January 30th, 2018 @ 12:38 PM

  13. Thomas Helmrich
    Thomas Helmrich

    PORT SET; SSL OFF = FAIL

    12:39:14 Sending request (989)
12:39:14 Handling request
12:39:14 Ready to run action (retry count: 0)
12:39:14 Clearing connection to mail.mydomain.de
12:39:14 Trying to connect to mail.mydomain.de on port 587 (CFNetwork) with STARTTLS (not required)
12:39:14 Resolved hostname (mail.mydomain.de).
12:39:14 Successful connection.
12:39:14 Ready for reading.
12:39:14 S: 220 mail.mydomain.de ESMTP Postfix
12:39:14 C: EHLO mydomain.de
12:39:14 S: 250-mail.mydomain.de
12:39:14 S: 250-PIPELINING
12:39:14 S: 250-SIZE 26214400
12:39:14 S: 250-ETRN
12:39:14 S: 250-STARTTLS
12:39:14 S: 250-ENHANCEDSTATUSCODES
12:39:14 S: 250-8BITMIME
12:39:14 S: 250 DSN
12:39:14 C: MAIL FROM:<thomas@mydomain.de> SIZE=7600
12:39:14 S: 530 5.7.0 Must issue a STARTTLS command first
12:39:14 Error: Unexpected return code 530 (expected 250):
“5.7.0 Must issue a STARTTLS command first”.
12:39:14 Error code: 2000
12:39:14 Failed action (0). Reset observed read/write timeouts: 8/8

12:39:14 Handling reply

    January 30th, 2018 @ 12:39 PM

  14. benny
    benny

    This is likely because port 25 is reserved for communication between server and not between client and server. This just fails in weird ways (MailMate cannot know this, but I guess it should complain itself when it cannot use the provided username/password -- which implicitly means the user expects authentication to happen).

    January 30th, 2018 @ 12:40 PM

  15. Thomas Helmrich
    Thomas Helmrich

    And Port not set & SSL on see my first post

    January 30th, 2018 @ 12:41 PM

  16. Thomas Helmrich
    Thomas Helmrich

    BTW: Username & Password was provided in each test

    January 30th, 2018 @ 12:42 PM

  17. benny
    benny
    • State changed from new to accepted

    Thanks, as noted further above I think we found the problem.

    I'll note this as a feature request: “Do not try to connect if a username is provided for an account while the server does not allow authentication.”

    January 30th, 2018 @ 12:44 PM

  18. benny
    benny
    • State changed from accepted to fixcommitted

    I changed the code such that sending would fail before trying to send -- and a more useful error message is provided.

    January 30th, 2018 @ 12:58 PM

  19. Thomas Helmrich
    Thomas Helmrich

    Thanks, too!

    January 30th, 2018 @ 02:02 PM

  20. benny
    benny
    • State changed from fixcommitted to fixreleased

    March 13th, 2018 @ 12:54 PM

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