iPhone and implicit SSL not working together

[sfulwood]

Having an issue with the iPhone connecting to Ability mail version 2.70. Implicit SSL is running on port 465. The Ability smtp logs show a connection from the iPhone, however the mail never leaves the mail box. Do you have any suggestions on what the issue could be or what to check next.

Thanks.
Scott

[Code Crafters]

Does your iPhone work normally on port 25 without SSL?

If so, then please email me at chris@code-crafters.com with:

1) details of any errors given on your iPhone
2) also send me the appropriate SMTP log explaining which IP or email addresses in the logs are related to your iPhone access and I'll have a look for possible causes. If you can, enable debug logging for SMTP, access again and send me that log which will contain much more detail. However, make sure you disable SMTP logging as soon as you're done as this will very quickly generate many MBs of log files if left on.

[robwaite]

I'm not using SSL but my iPhone works great with Ability when using IMAP and SMTP. It does take a while to initally connect when you first setup the mail server settings on the phone but works flawlessly afterwards. I've not tried SSL however.

[Code Crafters]

Looking at the logs you emailed me, the mail between the email addresses you mentioned was successfully received. However, the error on the phone shows a sending failure but this could either be an intermittent connection problem or could be a different account that failed since the IP given points to a mail server giving the a different welcome message than the AMS default welcome message. See below:

220 <yourdomain> ESMTP Service ready

If you have changed the AMS welcome message to this then it’s probably just an intermittent connection fault with the iPhone but the connection was made and the mail delivered into the AMS SMTP fine anyway. Note also that the time on the phone is about 2 hours earlier than the mail was received in the log, in case there was no time zone difference and this and the log show different sending events.

P.S. I also use my iPhone to check my emails from our Ability Mail Server too and have no problems accessing. If you install iTunes you can use the syncrhonise tool to automatically add all your accounts from your outlook then usually you just have to go in and set the passwords for each account (incoming and outgoing mail server for SMTP authentication) since the synchronisation must not be able to send those.

[sfulwood]

Hello Chris,

No, the welcome message has not been changed. We would not have any reason to do that.

I thought it might be a connectivity issue with the iPhone also, but we have three of the dang things here and each of them has the same problem. They can receive messages on their office account, but they cannot reply to those messages.

In addition, it seems that webmail is acting the same way. I can connect to webmail from outside of our network (from my house, for instance) I can see my office messages, but when I try to reply I get the message, "Account not local, relaying disallowed"

We have checked the settings in the server and believe them to be correct. What else would you recommend I look for?

Thank you in advance,

Scott

[Code Crafters]

If the welcome message doesn't say Ability Mail Server when you open a command prompt (Run: cmd) and type "telnet <mailservername> 25" then the IP is wrong or another mail server is using the port on that IP; either way you're talking to the wrong mail server.

As for the relaying disallowed error, this simply means that you have SMTP authentication enabled (as you must for security) but haven't configured your mail client (e.g. outlook) to log into the outgoing mail server (seperately to the incoming mail server) for SMTP authentication. In outlook account settings, press the More Settings button and go to the Outgoing Server tab to select logging into the outgoing mail server with the same login details as used for the incoming mail server.

Overall, it seems to be wrong settings for incoming and/or outgoing mail servers on your clients that is the problem. If you email me your mail server domains to chris@code-crafters.com I'll check that the basic ports are properly accessible from the Internet.

[sfulwood]

Chris,

When I run telnet from the AMS server I get:
220 radissonroc.com ESTP (Code-Crafters Ability Mail Server 2.70)

However, when I run the same command from any other computer on our network The command window goes blank (all typing disappears) and all I have is a flashing curser in the upper left corner of the window. If I press the 'enter' key several times I get a a solid cursor for several lines down and the upper cursor continues to blink. (Does any of this help?)

I'm making the changes to the Outlook clients now and my tests from them are coming back positive.

I'm still hoping to get the iPhones working. We have three of them here and none of them work fully with our business accounts. They can still receive, but cannot reply to the business account messages.

[Code Crafters]

Telnet is a good test of whether a domain or IP is the correct one for you to use. If this doesn't come back with a welcome message from AMS then you probably need to alter this to get it working. Either your domain IPs, router or firewall aren't allowing the connections properly. If you use an Internet IP not an internal network IP then this should work from anywhere. Also, make sure you don't have IP restrictions on the services that are stopping the connections. Also, SPAM transaction delays on welcome message could delay the welcome message so check for that too.

If you send me your domain (i.e. the bit after the @ in your email addresses) to chris@code-crafters.com I'll check the MX records and connections for you.

1) You should have at least one domain you have purchased. Or you can get a free one from http://www.no-ip.com.
2) You then need to setup your domain as follows:

domain.com
A = your website IP
MX = mail.domain.com

mail.domain.com
A = your mail server Internet IP

3) Next you need to forward ports 25, 143, 110 etc on your router to your mail server LAN IP which needs to be a static IP.
4) Let any mail server ports through any server side firewalls.
5) Make sure no other mail server is running on the AMS computer (using telnet or the status page of the admin interface).

[sfulwood]

Chris,

According the firewall an incoming connection is allowed to the mail server. However, the mail server never respondes to the hello and closes the connection (see log extract below). The iPhone then times out trying to send. help!

Fri, 20 Nov 2009 14:15:26 -> 166.137.6.137 -> Success: Action=[Accept Connection], Details=[Port 465: Implicit SSL]
Fri, 20 Nov 2009 14:15:27 -> 166.137.6.137 -> Success: Action=[POP Before SMTP], Details=[tgenti@adissonroc.com]
Fri, 20 Nov 2009 14:15:27 -> 166.137.6.137 -> Success: Action=[Received Hello], Details=[Host=[10.33.117.239]]
Fri, 20 Nov 2009 14:15:27 -> 166.137.6.137 -> Success: Action=[Close Connection]
Fri, 20 Nov 2009 14:15:46 -> 166.137.6.137 -> Success: Action=[Accept Connection], Details=[Port 465: Implicit SSL]
Fri, 20 Nov 2009 14:15:46 -> 166.137.6.137 -> Success: Action=[POP Before SMTP], Details=[tgenti@adissonroc.com]
Fri, 20 Nov 2009 14:15:46 -> 166.137.6.137 -> Success: Action=[Received Hello], Details=[Host=[10.33.117.239]]
Fri, 20 Nov 2009 14:15:47 -> 166.137.6.137 -> Success: Action=[Close Connection]
Fri, 20 Nov 2009 14:16:45 -> 10.34.12.69 -> Success: Action=[Accept Connection], Details=[Port 465: Implicit SSL]

[Code Crafters]

The closing of the connection could be due to the SSL not being propely initiaised or the fact that the wrong HELO/EHLO is used. It is also possible that the iPhone providing an IP as it's hos may even be the problem. You can enable debug logging for SMTP temporarily, try again with your iPhone and send me the log to chris@code-crafters.com or via the forum if you don't want to hide your email addresses and IPs (which I recommend you do on the forum; edit your last reply if necessary). Make sure you turn debug logging off straight after making the new log though as this will quickly fill many MBs of logs if left on debug logging. I will then have a log at the more detailed log to try to determine what may be going wrong for you.