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iPhone, can receive but not send email with exchange server

I have been able to get my iPhone to read my incoming e-Mail from our exchange server at work. That is the good part. The down side is I can't get it to send mail. I have tried several option and my IT guy says IMAP is enabled, incoming works. I did see a possible solution on the main support page and that was unsuccessful. I had to turn off the SSL to get the incoming to work. I have tried the outgoing both on and off with the four authentication options. Maybe the port isn't default on my server?

Any ideas?

Thanks for any help.

DeepPurple.

iBook, Mac OS X (10.5.1), iPhone

Posted on Nov 30, 2007 11:08 AM

Reply
11 replies

Nov 30, 2007 1:13 PM in response to DeepPurple23

DeepPurple23,

Yes, it does. That is why servers use ports so they can do more than one thing. Ok, for outgoing he will need to allow SMTP for you through the firewall. I would recommend against using port 25, and instead recommend authenticating SMTP on either 465 or 587. Whichever port the server listens to for authenticating SMTP will also need to be allowed through the firewall.

Alternatively if he doesn't want to open ports on the firewall, VPN might be an option.

Hope this helps,

Nathan C.

Dec 4, 2007 6:34 AM in response to DeepPurple23

DeepPurple23,

Yes, a lot of networks filter port 25 as part of their efforts to prevent spammers from exploiting mail servers set up to the "defaults".

Is your IT guy requiring authentication for you to use Port 25? If not, the server is an "open relay", I would suggest doing a web search for SMTP open relay for a list of why that is not a good thing. If he is requiring authentications on port 25 when you are not at work, then it isn't an open relay, but still might be blocked on some outside internet connections.

Port 25 is good for accepting email from other email servers, but not good for relaying without authentication.

That is why typically mail servers are configured to accept mail going to them on Port 25, but require authentication and a different port when accepting mail to relay out.

One analogy is your mail server is like your mail room in an office building. If you drop mail off on the inside mail slot, they should postmark, stamp and forward it on. They know you have access on the inside (internal network), and so they don't require ID (username/password) to verify who you are. If you drop mail off from the outside, they want to know who you (username/password) are before putting the postmark and stamp on for you. If the mail you are dropping off is for people inside, then they might not require ID or even it be stamped.

Hope this helps,

Nathan C.

Dec 5, 2007 7:49 AM in response to Nathan C

Nathan C,

Thanks for the feedback. As I continue to go through this my IT guy is becoming *****, I think we've exceeded his knowledge base and since he doesn't know instead of learning he'd rather not help. In any event, I believe that our system requires authentication. For instance when I'm at home, I fire up Outlook (not outlook express) and enter my password. Once I've done that it runs just as if I'm in office. When in the office I must log on to the network during the boot process of XP, so I believe that he requires Authentication, let me know if I'm incorrect there.

I'm still stuck on the sending phase, the error message I get is that it can not connect to my mail server, so it sounds like it is getting in, as I tried changing the port to 143 and it said my password was missing, when I corrected it, I couldn't get in. My incoming port is set to 143 and the SSL is off in the iPhone, that is the only way it would work. I have tried the SMTP with SSL on and off and all four authentication options.

When I'm at home I'm accessing the network through the proxy server, with mutual authentication turned on and the authentication settings set to "basic".

So, do you think I'll be able to solve this or is it possible to use my personal sbc account smtp settings to send e-mail from the exchange set up in the iPhone? Maybe if I set it up as "IMAP" in lieu of "Exchage"?

Let me know what you think and thanks for all of your help.

Regards,

DeepPurple23

Dec 5, 2007 9:04 AM in response to DeepPurple23

DeepPurple23,

Authentication can occur at several different points. I will use an analogy of your work network to accessing a safe deposit box.

When you log onto your computer you are authenticating on that computer, and possibly the network. This is like getting permission to access the safe deposit box room by showing ID.

Authenticating with the mail server is done separately. If the server is a safe deposit box, then authenticating with the server is providing the key to the box.

I want to go back a second. You said having to enter a password each time you use Outlook at home on your computer, and then it works like you are within the office. Are you using VPN?

If so, VPN might be a solution to your issue.

Hope this helps,

Nathan C.

Dec 5, 2007 12:50 PM in response to Nathan C

Nathan C,

I was doing some digging around on the web, thanks to your comment to search for port 25 and why it is bad. I noticed that there were several individuals all with similar issues to mine. I believe your orginial thought about port 25 being a problem was right on, I tried one of the work arounds mention by entering "cwmx.com" as the mail server, port 25 and no user name or password with the ssl turned off. Worked like a charm. I can send and receive e-mails from my work account now without issue. The post mention that this will only work on EDGE and probably not WiFi, but for me that is not an issue and it gives me everything I need in a smartphone, contact and calendar sync, with Outlook and now my e-mail from outlook as well.

Thanks for all of your help, I'm sure that it will irrate my IT guy to know that I solved it without his help. 🙂

DeepPurple23

iPhone, can receive but not send email with exchange server

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