I cannot for the life of me get imap over ssl working in exchange 2003. I have went as far as installing an existing cert we use for owa for imap. I enabled SSL/TLS option under authentication in the properties of default imap settings and I have tried requiring a secure channel and not under connection, which is also in the same area. I ran netstat -an on the server and it says it is listening on 993 and I cannot telnet to it. I can telnet to 143. My settings on the outlook 2010 client are incoming server is at port 143 and outgoing server port is 993. I just can't get this to work for whatever reason. Any help is much appreciated. Oh, and I am trying this on the local lan, I am not behind a firewall yet. Any help is much appreciated, I have tried everything I know of, including restarting services and disabling symantec endpoint security to no availability. Thanks in advance.

I suppose you've looked at articles like this? http://www.petri.co.il/how-to-enable-imap-access-to-exchange-mailboxes.htmPlease mark as helpful if you find my contribution useful or as an answer if it does answer your question. That will encourage me - and others - to take time out to help you.

I have seen that article and read through the whole thing yesterday ;) I just have no idea what could be blocking it. I am going to look at symantec endpoint on exchange again, just to make sure I didn't miss anything.

I made sure Symantec wasn't an issue. I turned up logging on imap services and am getting, event id:1008 which says connection attempt from 'ip' was rejected because the server is configured to have all access take place on a secure channel. I have no idea where to look now.

My settings on the outlook 2010 client are incoming server is at port 143 and outgoing server port is 993. Hi, Your incomming server should be configured with port 993 and not the outgoing one (SMTP)Martina Miskovic

Hi Martina, Thanks for the help. Under imap4 properties in ESM, what does the tcp port 143 mean? I tried using that for the outgoing server in my mail client and it didn't work? The standard smtp port 25 does work. Is there anyway to change outgoing mail server port for just imap users for those working outside of the office? I don't want to open up port 25 to the whole world on my firewall. Or is there a way to encrypt the outgoing server for just imap users? Let me know, Thanks, Bob

Hi, Can't tell you what SMTP Settings you should use, but I would recommend you to create a new "Default SMTP Virtual Server" for IMAP Clients with a port 587. That one is usually allowed in firewalls. May I ask why you need this? Can't the user connect with RPC over HTTPS? (So much better than using IMAP) IMAP 143 - Unencrypted Connection/plain text (=not recommended)Martina Miskovic

The user is on a mac :( Entourage I believe doesn't support rpc over https, I do have rpc over https setup for my windows users. So, basically, with the setup now, incoming email is encrypted and not encrypted for outgoing correct? I am wondering if I can just create a new smtp virtual server and make that secure using ssl and use 993 for that outgoing port, is that possible?

Ok, Thanks for answering that! You can configure Entourage to connect with https and webdav. Not exacly the same as rpc over https, but it should work.Martina Miskovic

Thanks for that, can you tell me what port 143 is for exactly under the imap virtual server? I am confused with this port, because for SSL it is set for 993 (incoming mail) and I created a new SMTP Virtual Server with it's own ip and gave it port 587 (outbound email). I just don't know where port 143 plays into this.

Thanks for that, can you tell me what port 143 is for exactly under the imap virtual server? I am confused with this port, because for SSL it is set for 993 (incoming mail) and I created a new SMTP Virtual Server with it's own ip and gave it port 587 (outbound email). I just don't know where port 143 plays into this. Hi, Port 143 is "normal" IMAP and 993 is IMAP over SSL (IMAPS). You will not use port 143.Martina Miskovic

Gotcha. So as a test for imap anyway since I wanted to keep my options open I added that additional smtp virtual server, gave it another ip address. It is strange, some messages send while others get stuck in the queue. I can't figure that out as to why. I used port 587 for the second smtp virtual server and gave it a different ip address as well. The default smtp virt server was left unassigned for the ip and then I tried assigning it the original ip addres. Very strange, like I said, some mail made it through and some didn't while that second smtp server was enabled.

Hi, I can't come up with any reason or resolution for your problem. The settings for your new SMTP Virtual Server seems correct to me Test if if works with Outlook. If it does, then it's a problem with Entourage. I have now knowledge about that version.Martina Miskovic

Hmmm...Everything seems like it is working now, strange. I will test it out. Thanks for all the help, I appreciate it! BB