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SMTP connector doesn't leave emails in "Sent Items" anymore

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  • Hi!

    It's happened on our Exchange 2007 server after SSL certificate update (the old one  expired). SMTP connector (for some reasons we are using port 587, not a 465 but I forgot why) is able to receive and forward emails (other mailflow, IMAP, is alright too) but don't leave copies of sent messages in "Sent Items" folder anymore :( It's 100% my fault (I'm not a pro Exchange admin) but I can't figure out what's wrong with my setup. New certificate, I'm 100% sure, installed for SMTP protocol (I've used something Enable-ExchangeCertificate -Thumbprint [my_cert_thumbprint] -Services "IMAP, POP, SMTP, IIS" 

    Could you please forward me to the right direction or give some advises?

    Thanks, Sergey


    WBR, SeNS

    15. března 2012 15:26

Všechny reakce

  • The send connector on Exchange has nothing to do with the Sent Items on your client for email.
    The only reason you would be using another port for email would be if the recipient is expecting email on that. As the internet expects email on port 25, that means you must be using a smart host.

    You are going to have to be more clear on what is or is not happening.

    Clients send email and the email doesn't go in to Sent Items? How are they connecting? POP3, SMTP, Outlook, Outlook Anywhere? Does the same problem occur in OWA?

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    15. března 2012 17:48
  • What do you mean by "nothing"??? OK, may be not a connector itself but some part of Exchange server.

    And, of course, I meant (in my post) the Exchange "Sent Items" folder, not a local. As I've already described before, it's happens for SMTP connector only (still don't understand why you mentioned POP3 and Outlook ???).

    OK, I'll try to make it 100% clear:

    - if I sending email using Outloook, connected via IMAP, or from Outlook Web Access, everything is allright, sent email appears in "Sent Items" mailbox folder on the Exchange side

    - if I send email using SSL SMTP, email is delivered correctly but email copy is not appears in the "Sent Items" Exchange mailbox folder.

    That stuff happens after SSL certificate update (actually, reinstallation).

    P.S. And, of course, local "Sent Items" (in Outlook or Outlook Express or ... or ...) is OK (it's a server-side problem, not a client!)


    WBR, SeNS

    15. března 2012 18:18
  • I mean absolutely nothing - the Send Connector has nothing to do with the sending of emails from the client to Exchange. Send connectors are for sending the email from Exchange to the recipeints server - the server to server communication.

    Sent items is a client issue, not a server issue. I mentioned POP and Outlook because it isn't clear what is happening. If it works correctly in OWA, then the problem is NOT Exchange.

    If you are using a non-MAPI client - so that is anything other than Outlook configured with an Exchange account (So Outlook Express or other IMAP/POP3 client) then the transfer of the email to the Sent Items folder is a client issue. If the email is being sent correctly, then Exchange is doing what it is asked to do.

    Being picky - IMAP doesn't send email, it is just a way of accessing the mailbox. To send email from a client that is accessing the email via IMAP requires SMTP. As you have said that is working correctly, that would appear to indicate everything is working as it should.

    Therefore what is different in your eyes between "IMAP" and sending email using SSL SMTP?

    If you send email just through SMTP from something that isn't connecting to the mailbox (like a script) then that message will not appear in the Sent Items because the email is just being "bounced" off the server.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    15. března 2012 18:44
  • Simon, you you really Exchange MVP? Or may be my English so bad and you can't understand my very simple question?..

    As I've said (one more time!), BEFORE changing SSL certificate everything works fine: SMTP connector successfully received email, relayed it to the destination server, AND SAVED copy of message into my Exchange mail box, to the Sent Items folder (on server!)

    Now it's NOT WORKING, Exchange didn't copied relayed message to the Sent items folder. 

    Client side settings HAVE NOTHING TO DO with it; actually, there are NO settings for that in Outlook or Outlook Express. 

    I'm using two different Outlook on two different PC for my tests, one directly connected to Exchange, another connected via SMTP/POP3, also I'm using OWA.

    So, my question is: how to restore/recover previous Exchange server behavior to save relayed mail to the sent items folder in Exchange mailbox.

    P.S. I'm 100% sure it's not a client side issue and 99.99% sure it's because of SSL certificate change. Also, I'm not a professional Exchange administrator; server works very seamlessly during 3 years but damn SSL certificate is expired this March :(


    WBR, SeNS




    • Upravený SeNS 15. března 2012 21:16
    15. března 2012 21:08
  • On Thu, 15 Mar 2012 21:08:43 +0000, SeNS wrote:
     
    >Simon, you you really Exchange MVP?
     
    Yes, he is. Are you really an Exchange administrator?
     
    >Or may be my English so bad and you can't understand my very simple question?..
     
    Your question was simple. So was the answer. However, you're assuming
    the changing the certificate has something to do with a mailbox
    folder. That's like say that a flat tire is preventing your car from
    starting. After all, it used to start before the tire went flat, but
    it hasn't started since then.
     
    >As I've said (one more time!), BEFORE changing SSL certificate everything works fine: SMTP connector successfully received email, relayed it to the destination server, AND SAVED copy of message into my Exchange mail box, to the Sent Items folder (on server!)
     
    If the Exchange server was acting as a SMTP relay the message never
    went anywhere near your mailbox. The only way a message would end up
    in your mailbox's sent items folder is if the message was deliverd to
    the mailbox and there was a client-side inbox rule that send the
    message.
     
    >Now it's NOT WORKING, Exchange didn't copied relayed message to the Sent items folder.
     
    Exchange NEVER DID. See, putting things in UPPER CASE proves my point!
     
    >Client side settings HAVE NOTHING TO DO with it;
     
    YES IT DOES! See? There's that UPPER-CASE thing again.
     
    >actually, there are NO settings for that in Outlook or Outlook Express.
     
    Really? Outlook has no way to create a client-side inbox rule? WOW! A
    lot of people will be very surprised to hear that.
     
    >I'm using two different Outlook on two different PC for my tests, one directly connected to Exchange, another connected via SMTP/POP3, also I'm using OWA.
    >
    >So, my question is: how to restore/recover previous Exchange server behavior to save relayed mail to the sent items folder in Exchange mailbox.
     
    Exchange never did that so it isn't possible to recover/restore.
     
     
    >P.S. I'm 100% sure it's not a client side issue and 99.99% sure it's because of SSL certificate change.
     
    That 0.01 can be a real b1tch, can't it?
     
    >Also, I'm not a professional Exchange administrator;
     
    Yeah. We kinda got that.
     
    >server works very seamlessly during 3 years but damn SSL certificate is expired this March :(
     
    Go repair the flat tire and I'm sure your enginge will start again.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    15. března 2012 21:46
  • You guys are ridiculous, can't follow the simple Aristotle logic! And YES again, I'm not a professional Exchange administrator, whats why I'm here.

    1) I did not change anything on the client side (for some reasons I'm using SMTP/POP3 connection to that Exchange server from home). Simple - I didn't touch ANYTHING.

    2) Before certificate change, any message sent from my home Outlook, appears into "Sent Items" mailbox folder on OWA and another Outlook, connected to Exchange via RPC (usual way for Outlook)

    3) After certificate change, that not working anymore.

    Nothing ELSE was changed, PERIOD. What is not clear to you? I don't know anything about flat tires, just called AAA - and they DO the job, not a start useless blaming. And what to do with the inbox rules? How you can put sent email to the Exchange mailbox folder "Sent items" by the Outlook local rule? Please tell me...


    WBR, SeNS

    P.S. If you have no knowledge, better do not reply... 
    • Upravený SeNS 15. března 2012 22:41
    15. března 2012 22:40
  • What you have described is not possible.

    If you are accessing your mailbox with POP3 then sent items will be stored in the local copy of the mailbox ONLY. They will not appear in the Sent Items of the mailbox on Exchange.

    That means either

    a. You were using IMAP.

    b. You were using Outlook Anywhere

    c. You were using a combination of the above and that is no longer working.

    Changing the SSL certificate could have stopped both IMAP and Outlook Anywhere from working as the SSL certificate was no longer trusted.

    If you are seeing the full mailbox as it appears in Exchange, complete with folders etc, then you almost certainly were not using POP3, as POP3 doesn't bring the same folder structure down from the mailbox.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    15. března 2012 23:04
  • What you have described is not possible.

    If you are accessing your mailbox with POP3 then sent items will be stored in the local copy of the mailbox ONLY. They will not appear in the Sent Items of the mailbox on Exchange.

     What is impossible? Have you read what I already wrote 3 times? I'm sending using SMTP, with SSL authentification (using same credentials as POP3 blah-blah) using my existing Exchange email address and domain user credentials. And I'm accessing NOT using POP3 but Outlook via RPC, and OWA via https (SSL).
    I'm not complaining about POP3 access and my local "Sent Items" (I'm not an idiot!) but remote, on the server side.


    WBR, SeNS

    15. března 2012 23:47
  • I directly quote:

    "for some reasons I'm using SMTP/POP3 connection to that Exchange server from home"

    Now you say you are using Outlook Anywhere. Which is it?

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    15. března 2012 23:49
  • Actually, don't bother answering, I am dropping off the question. I don't need this.

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    15. března 2012 23:49
  • Fellows, I'm an accidental Exchange admin myself, so please be patient...

    If I have IMAP/SMTP client and using SMTP on the Exchange server for sending, even though I'm authenticating for SMTP connection, Exchange server will _not_ locate my mailbox and copy the outbound email to Sent Items on the server. It is client's responsibility to move messages between folders (and into Sent Items) unless the client is full MAPI client. Is this statement correct?

    Cheers


    -= F1 is the Key =-

    17. března 2012 7:53
  • On Sat, 17 Mar 2012 07:53:57 +0000, S. Pidgorny wrote:
     
    >
    >
    >Fellows, I'm an accidental Exchange admin myself, so please be patient...
    >
    >If I have IMAP/SMTP client and using SMTP on the Exchange server for sending, even though I'm authenticating for SMTP connection, Exchange server will _not_ locate my mailbox and copy the outbound email to Sent Items on the server. It is client's responsibility to move messages between folders (and into Sent Items) unless the client is full MAPI client. Is this statement correct?
     
    Unless there's a server-side Inbox rule it's always the client's job
    to manage that stuff.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    17. března 2012 20:42
  • Sergey, please contact Microsoft support for further assistance.  Obviously there is a disconnect here and the forums aren't the correct medium to get your issue sorted out.  I am locking this thread as it has turned abusive.


    Mike Crowley | MVP
    My Blog -- Planet Technologies

    23. března 2012 4:07