"Cannot Connect To Server" Error

Posted on 2008-10-27
Last Modified: 2010-01-08
I didn't see this specific problem discussed, at least with my particular issue. I am able to setup my Exchange account without any problem... I do get a message pop up twice saying that my SSL configuration could not be verified, or something to that effect, and I just hit accept twice and the account is setup successfully. I'm guessing this is because we have self-signed certificates or something to do with that (from what IT has told me). However, after a few hours goes by, I get the "cannot connect to server" message. I figured out that I can resolve this by going in and checking SSL to 'no' and then my account starts magically sync'ing up again. Several hours later (up to a day sometimes) I get the error again. I go back in and switch SSL to 'yes' and it sync's back up again. Basically I keep having to go back in to my settings and flipping it on or off to get it to sync.

Does that make any sense? I read somewhere where you could install a certificate on the phone itself, but I don't know much about that or what I need to do exactly. Has anyone been able to configure Exchange on the iPhone so that it works seamlessly without any issues or disconnects? This is my one beef with the iPhone and I know there are countless posts out there with a million different ideas for fixing the problem but none appear to have been successful. Any help or direction would be greatly appreciated!

By the way, we're running Exchange '03 with SP2 if that makes any difference.
Question by:L1Technology
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Ok, quick update. I figured out how to install a certificate on my iPhone by going to OWA and sending the certificate as an attachment. Followed the steps here:

I don't know what that's going to do if anything, but just wanted to mention it.

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Quick update... installing a certificate doesn't seem to have any effect at all. Also tried setting up the Exchange account through the iPhone utility and no luck there either, still get the "cannot connect to server" message after a few hours.

One thing I did notice this morning was I had gotten that message overnight and was connected to my home wireless network. I just left it alone and as soon as I drove away and lost the WiFi signal, the Exchange server connected again. So now I've got WiFi turned completely off to see how long I can stay connected.

Any help or comments would be appreciated, I'm getting to the bottom of my list of possibilities and don't know what to try next. I'm pretty much resigned to the fact that this is an Apple Firmware issue since so many other people are experiencing related problems.

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Anyone? Hello?

Accepted Solution

L1Technology earned 0 total points
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Well, after the overwhelming contribution from the "Experts" (lol), I think I've resolved my own issue thank you very much. I hope my talking to myself can at least help someone else going forward that is dealing with the same issues as me. Come to find out we have multiple DNS setup with Exchange 2003 and apparently after a length of time (few hours, up to a day) it would switch to a different address or something to that effect and lose it's connection altogether.

I've resolved this by entering the primary IP address of our mail account. In most cases you can find this by pinging the exchange hostname (i.e. or asking your email admin and then entering that IP in the server field within your account settings on the iPhone. That's seemed to resolve my issues after hours of research and trying different things. Hopefully this is of help to someone, at least more than Experts-Exchange was for me.

Expert Comment

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Well - looks like you are the expert now. Thanks for posting what you discovered. My boss just started having this problem last week. I am going to give your solution a try. Thanks again!!

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