"Connection to server failed."

This occurs with a MobileMe account?

If so, when connected via an available wi-fi network, when connected via the cellular network, or both?

I suggest deleting and recreating the account on your iPhone.

I have to restart my iPhone 3G whenever I want to check mails, otherwise I get the "Connection to server failed" - and no mails are being fetched (using IMAP and MobileMe). This is also discussed in this thread (which is closed):

http://discussions.apple.com/message.jspa?messageID=7845987

Worse is that it started to happen more often after the version 2.2 update. Before I could sometimes not connect to the internet after a while (through among other things, Safari), and had to restart but I could still check my mail. Now mail fails to deliver almost every time I check - no matter the connection type (3G, GPRS, Wi-fi). Spinning "asterisk" of death... 🙂

Unfortunately, I don't see any solution to this (especially when looking at the thread mentioned above)... Must wait for an update which - hopefully - will resolve the problem.

Sigh...

I am having the same problem. Take a look here: http://discussions.apple.com/thread.jspa?threadID=1811260

I have tried many things and still no fix. I noticed this with Update 2.2. They need to fix this ASAP. The mail is unreliable. I might go to using a blackberry.

I had the same problem, but the thread triggered some investigating. My server is password verification. The new update appears to have shifted verification to something else, MD5 Challenge Response. Go to settings, account, advanced, authentication, and change to password. Make sure the password is correct. Mine then instantly downloaded. Hope that helps.

maclank,

Have you already tried resetting network settings?

To do so, navigate to Settings > General > Reset.

Hope this helps,

Raleigh

Does anyone know while using Safari I get the web site pulled up, the screen goes black and returns to the home screen?

This means Safari has crashed.

Have you installed firmware update 2.2?

If so, go to Settings > Safari.

Select Clear History, Clear Cookies, and Clear Cache.

Next do a reset, which is done by pressing and holding the Home button and the sleep/wake or on/off button simultaneously until you see the Apple logo and then release - ignoring the slide to turn off prompt when doing so.

@AlanBrooklynNYC:

My server is also password protected, but nothing had changed since the latest update - I still have 'password' as verification and the passwords are also correct since I - whenever I can get the connection – can check mail successfully.

I also investigated and had a nagging suspicion that it could have something to do with a network setup involving several airports. I've had some troubles regarding syncing with third party apps while connected to a network involving two or more airports (where the apps are confused about what specific airport they should communicate with my Powerbook through), but I've also had the same mail troubles regarding connection failure while running my iPhone in 3G and GPRS mode, so I'm running out of clues here...

I'm having the same problem. Interestingly, I could send mail with no problems for the first two weeks and then started having problems over the weekend. I called my email host, and they said to turn off SSL authentication (it was on) and to enter my password in the outgoing mail server. I did all of these things even though it had worked fine for the previous two weeks. I was able to send a couple of emails that were in my Outbox. A couple of hours later: same problem again. This is crap. iPhone is a great toy. Garbage for personal productivity. I never had these issues with Blackberry. I'm about to go back.

I've been having this problem recently, and oddly enough, it only happened once I added a new MobileMe account under my MobileMe Family plan. With that second account enabled, I started getting the "connection to the server smtp.mac.com failed" or "connection to the server smtp.me.com failed" -- which I found odd since this was an Apple account designed specifically to work with the iPhone.

Anyway, my solution is a bit tedious, but it seems to have worked.

First, sync your phone with iTunes just to make sure you have all the latest applications and music that you might have downloaded to your phone copied over to iTunes. Once it's done syncing, in iTunes, click the Restore button to completely restore the iPhone to its factory settings. When asked, DO NOT restore your iPhone backup (because that will just restore the problem settings you had before). Choose instead to "Set up a new iPhone" and let iTunes go through the steps to do that. If you have a .Mac or MobileMe account, keep the check boxes selected to sync your mail, contacts, and calendars to your phone. (This will restore the default over-the-air syncing that goes with MobileMe.) You'll need to reselect all your playlist, photo albums, videos or whatever you have specific to your phone. And of course, because it will be copying all the files as if the phone were brand new, it will take a good 15 - 30 minutes to copy everything over. (I have a 16 GB phone, and it took about 30 minutes to copy about 13 GB of media.)

Lastly, once everything has synced to the phone and you can disconnect it from iTunes, you'll need to go to your iPhone and customize it -- choose your ring tone, move app icons around, select favorites in your phone list, etc. If you are using a .Mac or MobileMe account, be sure to go into the Settings for Mail, Contacts, Calendars, select the account, and turn on syncing for contacts, calendars, and bookmarks (unless, for some reason, you don't want that).

Since then, I've been asked to enter my password once for my email account and to enter the password to connect to my wireless network, but otherwise, everything has worked fine. No more "connection failed" messages. Hurrah!

I hope that works for some other folks out there. If it DOESN'T solve the problem for you, please post back here and share how your setup might be different from mine so maybe we can identify specific problem areas. It's Tech Support, Web 2.0 style! Everybody contributes! 🙂

Okay, so after all of that, my mail worked for about 2 hours after I posted that message, and then it once again started giving me the "connection failed" message.

BUT, I went to the MobileMe support page and started a chat with a support representative, and +she actually fixed it!!+

It's been two days, and no problems. I've been waiting to post this just to make sure that everything is still working, and I've sent a LOT of test messages from my iPhone MobileMe account in that time and they've all worked fine. No more errors.

So, if anyone is still having this problem -- at least with MobileMe -- I highly recommend getting in touch with MobileMe support at http://www.apple.com/support/mobileme/ Under "Get help with MobileMe," I selected "MobileMe Mail" and then "Other Mail questions." Click on Chat Now and then describe the problem to the support rep. My rep had me do some stuff with turning off Push, deleting my MobileMe mail account from my iPhone, adding it new, and then she did a few things on her end with the account.

As I say, since then, I've had no problems whatsoever, and it's been two days now. I don't know if contacting iPhone support can help in a similar way with gmail, Yahoo!, or Exchange accounts. But if you are having trouble with one of those, the Apple support page says that iPhone users have two years of support (as long as you still have an active wireless plan on your phone), and so you can call:

~ U.S. iPhone technical support: 1-800-MY-IPHONE (1-800-694-7466)
~ Canada technical support: 1-800-263-3394

Or go to http://www.apple.com/support/contact/phone_contacts.html to find phone numbers for other countries.

Hope this helps!