iPhone 3G email setup and rough edges

I finally had a chance to play with an iPhone 3G. Unfortunately, it wasn't mine it was my managers. She's giving it a test run for our company since her Blackberry died which she hated anyway.

I won't tell anyone anything by saying it is fantastic. Blackberry has to be crapping their pants now if they weren't already. The ads that Blackberry has running are laughable at best. Can you imagine watching a video or browsing the web on the stupidly small screens they have even if they are the same resolution as the iPhone's?

Activesync setup for Exchange with this thing was a bust and an exercise in frustration. However, I think this is an Exchange 2003 issue and not the iPhone at all. I eventually had to back down and use the IMAP email function to retrieve email and forgo the automatic sync of calendar and contacts and use the iTunes sync to accomplish this. Unfortunately, this is where a glaring issue reared its ugly head.

Syncing your calendar and contacts with Outlook using iTunes simply doesn't work. Looking around on the forums at Apple, I'm not the only one. It appears the update to the 2.0 firmware and iTunes 7.7 broke something. The system, when you initiate a sync, literally sits there sync'ing for 20-30 minutes. When done, the best you get is the contacts and no calendar. On top of that, I had bookmarks set to sync and bookmarks weren't there either.

Depite the numerous posts I see no official response from Apple which is disappointing. Some acknowledgement of the problem and that it is being worked on would be nice. I could be wrong but there is a pattern of Apple not admitting to flaws. For instance, whenever I get asked to update iTunes, I can never seem to find a change log or release notes that describes precisely what is and isn't fixed or changed between the new version and the old.

Finally, I'll just add my two cents on how I setup SMTP sending for the iPhone since numerous articles don't seem to address this scenerio or are just frankly more complicate than necessary.

Scenerio:

You have an Exchange server behind a firewall. You don't allow SMTP communications from the outside to it directly. All SMTP traffic has to pass through a spam filter of some sort. The SPAM filter can't be used as an SMTP server for outside email when the from address equals your own domain name.

Problem:

You can't send SMTP to yourself or anyone else using your spam filter because all email addresses with your domain are INSIDE the network and so sending from the outside with an internal address is presumed to be spam.

Exchange SMTP services (windows SMTP actually) doesn't allow you to restrict traffic to an IP address and allow all other IP's only if authenticated. If you restrict by IP, you have to specify all IP's that can send through it (not possible for the random IP's assigned to the iPhone obviously). If you require authentication, all SMTP senders need to authenticate and most spam filters (at least mine anyway) cannot authenticate to send. It just opens a port and starts spitting out email.

Solution:

• Keep the internal Exchange server restricted and available only to the spam filter like you have now.
  
  
• Create a new SMTP server service on your exchange server and designate the port it uses as something other than port 25. Preferably something up high and it should be above port 1024.
  
  
• Change the authentication settings for the SMTP service to allow only authenticated users to send email. You'll have to choose whether to require encryption or not.
  
  
• Modify your firewall to allow sending to this new port on your exchange server.
  
  
• On the iPhone, go into the email settings for the IMAP account and at the bottom there is a place to change the outgoing server settings.
  
  
• Once selected, you'll see at least two accounts there (usually, there may be more). One is your SMTP account you setup and the other is AT&T's SMTP server. Normally, you could use AT&T's when on the EDGE network but the spam blocker prevents this. (incidentally, allowing multiple sending SMTP services is brilliant, it just doesn't work this time)
  
  
• Modify you SMTP account settings to point to your exchange server but near the very bottom of the screen you do this, change the port settings from port 25 to the port you selected when you setup the new SMTP service on your server.
  
  
• Try it and if all is well, it should work.

Hopefully this is helpful. Good luck!