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Trouble sending from one IMAP account

#517

The following error log is taken from the activity viewer. What is the source of the error? I think it may be an expired SSL server certificate. See below.

The following recipients were rejected by the SMTP server:
twadds@mac.com

Unexpected return code 550 (expected 250):
“5.7.1 Unable to relay”.

Tip: Open the Activity Viewer (⌥⌘0) before retrying. The SMTP log file might provide additional information.

C: QUIT
S: 221 2.0.0 Service closing transmission channel
Clearing connection to mail.mounthospitalpharmacy.com.au
Clearing connection to mail.mounthospitalpharmacy.com.au
Clearing connection to mail.mounthospitalpharmacy.com.au
Trying to connect to mail.mounthospitalpharmacy.com.au on port 25
Successful connection.
S: 220 mail.mounthospitalpharmacy.com.au Microsoft ESMTP MAIL Service ready at Mon, 2 Dec 2013 21:02:52 +0800
C: EHLO [10.1.1.16]
S: 250-mail.mounthospitalpharmacy.com.au Hello [106.68.69.109]
S: 250-SIZE 10485760
S: 250-PIPELINING
S: 250-DSN
S: 250-ENHANCEDSTATUSCODES
S: 250-STARTTLS
S: 250-AUTH
S: 250-8BITMIME
S: 250-BINARYMIME
S: 250 CHUNKING
C: RSET
S: 250 2.0.0 Resetting
C: MAIL FROM:andrew.twaddle@mounthospitalpharmacy.com.au SIZE=284
S: 250 2.1.0 Sender OK
C: RCPT TO:twadds@mac.com
S: 550 5.7.1 Unable to relay
Error: Unexpected return code 550 (expected 250):
“5.7.1 Unable to relay”. Error: The following recipients were rejected by the SMTP server:
twadds@mac.com

Unexpected return code 550 (expected 250):
“5.7.1 Unable to relay”.

Reported by Andrew Twaddle · December 3rd, 2013 @ 03:05 AM

State: new
Milestone: none
Assigned to: benny benny

Activity

  1. benny
    benny

    It looks like SSL is not enabled for the SMTP server. The server does not state any problem with this, but you could try enabling it for the SMTP account.

    An expired certificate should not result in this kind of problem.

    December 3rd, 2013 @ 11:55 AM

  2. Andrew Twaddle
    Andrew Twaddle

    Hi Benny thanks for your reply!

    Any idea what that error could be? I can only send email to email addresses outside my own domain when I am physically connected to my work network. If I am working remotely it will come up with an error message such as this every time.

    I appreciate any help you can provide.

    Love this client by the way I've been using it solidly for a couple of weeks and it feels like I've known it all my life and I can't imagine emailing without it.

    Many thanks again!

    December 5th, 2013 @ 12:35 PM

  3. benny
    benny

    Did you try enabling SSL for the SMTP server? Use “File ▸ Edit IMAP Account” to edit the account and then make sure SSL is enabled for the SMTP settings.

    December 5th, 2013 @ 02:16 PM

  4. Andrew Twaddle
    Andrew Twaddle

    It already was enabled. It was ticked anyway.

    No luck unfortunately.

    December 5th, 2013 @ 02:28 PM

  5. Andrew Twaddle
    Andrew Twaddle

    Sorry to bother you again Benny, but did you have any other ideas how I can get around this error?

    Many thanks.

    btw I love the new fantastical commands and other experimental features. Looking forward to 2.0!!

    December 23rd, 2013 @ 05:11 AM

  6. Andrew Twaddle
    Andrew Twaddle

    I'm sure I'm not adding anything here Benny but I just thought I'd refresh this ticket.

    here is a recent log from the Activity viewer.

    Can't get anything to work sadly

    C: QUIT
    S: 221 2.0.0 Service closing transmission channel
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Trying to connect to mail.mounthospitalpharmacy.com.au on port 25
    Successful connection.
    S: 220 mail.mounthospitalpharmacy.com.au Microsoft ESMTP MAIL Service ready at Tue, 7 Jan 2014 22:10:44 +0800
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-STARTTLS
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: STARTTLS
    S: 220 2.0.0 SMTP server ready
    Initiating SSL/TLS...
    Setup of SSL/TLS connection complete.
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: RSET
    S: 250 2.0.0 Resetting
    C: MAIL FROM:andrew.twaddle@mounthospitalpharmacy.com.au SIZE=313
    S: 250 2.1.0 Sender OK
    C: RCPT TO:twadds@mac.com
    S: 550 5.7.1 Unable to relay
    Error: Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. Error: The following recipients were rejected by the SMTP server:
    twadds@mac.com

    Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. C: QUIT
    S: 221 2.0.0 Service closing transmission channel
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Trying to connect to mail.mounthospitalpharmacy.com.au on port 25
    Successful connection.
    S: 220 mail.mounthospitalpharmacy.com.au Microsoft ESMTP MAIL Service ready at Tue, 7 Jan 2014 22:13:51 +0800
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-STARTTLS
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: STARTTLS
    S: 220 2.0.0 SMTP server ready
    Initiating SSL/TLS...
    Setup of SSL/TLS connection complete.
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: RSET
    S: 250 2.0.0 Resetting
    C: MAIL FROM:andrew.twaddle@mounthospitalpharmacy.com.au SIZE=313
    S: 250 2.1.0 Sender OK
    C: RCPT TO:twadds@mac.com
    S: 550 5.7.1 Unable to relay
    Error: Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. Error: The following recipients were rejected by the SMTP server:
    twadds@mac.com

    Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. C: QUIT
    S: 221 2.0.0 Service closing transmission channel
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Trying to connect to mail.mounthospitalpharmacy.com.au on port 25
    Successful connection.
    S: 220 mail.mounthospitalpharmacy.com.au Microsoft ESMTP MAIL Service ready at Tue, 7 Jan 2014 22:14:22 +0800
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-STARTTLS
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: STARTTLS
    S: 220 2.0.0 SMTP server ready
    Initiating SSL/TLS...
    Setup of SSL/TLS connection complete.
    C: EHLO [10.1.1.14]
    S: 250-mail.mounthospitalpharmacy.com.au Hello [124.148.81.97]
    S: 250-SIZE 10485760
    S: 250-PIPELINING
    S: 250-DSN
    S: 250-ENHANCEDSTATUSCODES
    S: 250-AUTH
    S: 250-8BITMIME
    S: 250-BINARYMIME
    S: 250 CHUNKING
    C: RSET
    S: 250 2.0.0 Resetting
    C: MAIL FROM:andrew.twaddle@mounthospitalpharmacy.com.au SIZE=313
    S: 250 2.1.0 Sender OK
    C: RCPT TO:twadds@mac.com
    S: 550 5.7.1 Unable to relay
    Error: Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. Error: The following recipients were rejected by the SMTP server:
    twadds@mac.com

    Unexpected return code 550 (expected 250):
    “5.7.1 Unable to relay”. C: QUIT
    S: 221 2.0.0 Service closing transmission channel
    Clearing connection to mail.mounthospitalpharmacy.com.au
    Clearing connection to mail.mounthospitalpharmacy.com.au

    January 7th, 2014 @ 02:17 PM

  7. Steve Mayer
    Steve Mayer

    Thought I'd chime in here.

    So, to summarize:

    When you're connected to your work network, you can send mail to users that exist outside of your work network.

    When you disconnect from your work network, but try to send mail via your work SMTP server, you get the 'Unable to relay' message from the SMTP server.

    When not connected to your work network, are you able to send email to users within the work email domain? (somebody@mounthospitalpharmacy.com.au)?

    Has this ever worked? It sounds like typical relay blocking in the SMTP server.

    January 7th, 2014 @ 07:35 PM

  8. Andrew Twaddle
    Andrew Twaddle

    Hi Steve,

    I think you are right. I can send to people from my own domain when not connected to the work network.

    I'll look into the relay blocking.

    Thanks for the tip

    January 9th, 2014 @ 11:40 AM

  9. Andrew Twaddle
    Andrew Twaddle

    All working now.

    Many thanks Steve.

    Benny please close this ticket.
    Cheers

    January 13th, 2014 @ 11:53 AM

  10. benny
    benny
    • State changed from new to resolved

    January 13th, 2014 @ 12:02 PM

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