Push Email Options for the iPhone

Since obtaining my 3G iPhone, I have been looking at ways to use push email on it. I thought I'd share my findings with you, in the hope it might aide your decision making when it comes to push email.


MobileMe

• It looks pretty and for a home user it is gold - you cant go past it. It's easy to use and "just works".
• I can't get my head around loading all my mail onto a server in the USA and hoping it doesn't go away. I like to control my email.
• A downside of a fully US hosted service is the timing of service outages. Middle of the day for us, middle of the wee-hours for them. It can be quite inconvenient.
• Lacks domain support, so I can't use name@mydomain.com - I'm stuck using me.com
• The price tag is rather high for each year compared to other solutions if all you want is push-email.

Yahoo Push Mail

• Yahoo supports domains, so I can use myname@whatever.com and not stuck with yahoo.com
• Is cheap - free for limited options, paid upgrades available that enhance functionality.
• Interface isn't as nice as MobileMe.
• The push mail sometimes has lengthy delays and mail comes in spurts.
• Supports Address Book push features, so updates to your contacts sync over the air in real-time.
• Overall it seemed to work rather well, however sending emails would fail from time to time.

Exchange 2007

• The iPhone support for Exchange is flawless.
• The performance of syncing was spot on with the iPhone - often the iPhone would get mail before the desktop Mac Entourage 2008.
• Using Mail 2.0 on your Mac in Exchange mode doesn't seem to work all that well. It seems to function more like IMAP then MAPI. I would have to press send and receive to get new messages.
• iCal isn't supported by Exchange Server as .ics files are not compatible with Exchange Protocols.
• Address Book on the Mac has features for Exchange but I cant get them to work with Exchange 2007 even with full debugging. I spent at least 12 hours on it with no success. The only way to integrate the Address Book is tell Entourage 2008 to sync the Address Book into the Exchange Server. You can change address data on your iPhone, in Entourage 2008 or within Address Book on your Mac and any one of those will update the others.

Kerio MailServer

• Kerio just released support for iPhone ActiveSync, so Kerio MailServer acts as an Exchange Server, meaning it works with the iPhone, without the need for Exchange.
• Kerio MailServer runs on Mac OSX 10.3+, Windows XP/2003/2008 and Linux
• Kerio has the fantastic ability that no other product has - the ability to run iCal and Exchange Calendaring together.
• Address Book syncing works correctly, it will also support Entourage 2008 in Exchange mode.
• They also have a Exchange Server Migration tool that is free. Three clicks all your contacts, mail and calendars are imported from an Exchange Server.

Conclusion
If your are a home user who wants all the features with Windows and Mac's around the house you can't go past MobileMe. It is one of the only cross OS syncing applications what works in Windows and Mac seamlessly. However, it is not cheap at over $100/year. If you only want basic push mail then Yahoo is by far the cheapest around, but it has it's flaws in not being 100% reliable. MobileMe and Yahoo are both great products but your data is hosted on their servers. That means you are at the mercy of both Internet congestion between the USA, as well as falling into outage times at 3pm-6pm here in Australia due to USA/AUS time difference for maintenance.

If you are a current Entourage user, connected to an Exchange server, your iPhone will work very well with it, however, you can't use iCal or Address Book to make everything sync. It all needs to be within Entourage & Exchange.

If you want to move to an Exchange server for the purposes of the iPhone, take a look at Kerio MailServer. It is much cheaper than Exchange, requires less resources and is fully compatible with the iPhone and Mac OS X. It's a perfect addition to a small business setup and much more flexible than Exchange. There is even a 30 day free trial available on the Kerio website.

Nice work! I had no idea about Kerio Mail Server, but it looks quite slick, supporting the iPhone via Exchange! Price is very affordable too.

Have you looked into Zimbra at all Maticks?

great info there! I'm still trying to find a leopard server solution (well at least until snow leopard gets here) I'll advise if anything comes of it

Kerio Mail Server works on Leopard Server!

I reckon 10.6 will have push email/contacts/calendars built in. Maybe even an upgrade to 10.5 will bring it.

that would be lovely...I'm just looking for a solution I can do myself without the $600 price tag...it's only for me and a few people that have addresses on my domain...c'mon opensource...well comeon Apple and allow a user-compiled php module to be used with the standard Apache install... |annoyance|

Would be awesome if MacTalk could start a service for its members for a monthly fee to offer things like @mactalk.com.au email addresses with push functionality.

Good post. There is a work around for this, if your personal domain is hosted on a mailserver you have control of. I'll give an example, based on what I did.

Warning: The following is quite technical. Unless you're in the same situation as me, and run your own mailservers, you're probably going to be SOL trying to do what I've done here. I can't take any responsibility if you screw up your mail by following these instructions either.

Firstly, some background. I have a domain, stupendous.net, which I host on my own server in a datacenter in QLD. Its nice and fast, I can run whatever I like, and until I had my iPhone I was perfectly happy with just running my own IMAP server on there.

When I got the iPhone I wanted push email for stupendous.net, but you can't do that. You can only fetch every 15/30/60 minutes, which drains the battery. So I worked out a better way.

There are two problems.

1) MobileMe doesn't accept mail for any domain other than me.com and mac.com.

Obviously the solution for me was to forward everything off my account to my me.com address. In my exim .forward file in my home directory, after all of the rules I use to filter mailing lists, I have

This happily sends on mail to me.com. The bonus to this is that they do additional spam checking on top of all barrage of spam filtering I do, so I've been getting very little spam in my account.

2) When sending mail from the iPhone, you cannot set the From: address to another domain. MobileMe requires you to send from a me.com or mac.com address.

The dodgy hack here was to configure another SMTP MTA on the iPhone and point it to my server, disable the me.com MTA, and then on my MTA I rewrite the From: address to my stupendous.net address. I only rewrite the From: address, so that bounces go back to my me.com address directly (its bad form to completely obscure the sender).

On my Debian system, it keeps the rewrite rules in /etc/exim4/conf.d/rewrite. So I added a new file there:

32_rewrite_domain:

It's numbered 32 to load after the exim4 default rule.

And thats it! If you look at headers for a mail sent from my iPhone, you'll see:

Not sure why I bothered obfuscating my email address, as it's pretty obvious. Oh well. Maybe it will confuse the spammers.

Its possible that some other company provides a sender rewriting authenticated SMTP server service. Hell, if you were to offer me money I'd be happy to set one up for you. :P Is there anyone who would be interested in an authenticated SSL SMTP relay with sender address rewriting?

Awesome, just the information I was looking for!

Check out mail2web.com as they now offer a 'personal exchange server for iPhone' which is free. Basically, you redirect your email to it, and it comes through instantly.

I didn't go with the free one, I went with the $5 per month one, but I can contest that it works well.

Gmail IMAP not a consideration or is it a different category altogether?

*nevermind, decryption is explaining to me over chat*

Not in order to enjoy the benefits of push. IMAP has to be fetched, so even if you have it fetched every 15 minutes, it could take you that long to receive a message, and will cost you in data and battery life.

[quote=chrome;578097]Good post. There is a work around for this, if your personal domain is hosted on a mailserver you have control of. I'll give an example, based on what I did.
/QUOTE]

Thanks for sharing, I run my own domain (well its a collection of domains now but anyway), and I'm still trying to decide how to run my mail.

I didn't realise me.com didn't support domains for mail, this is what I've been thinking about, but now I need to think some more. The MTA trick is obvious now you mention it. No actual iPhone here, so I haven't had a chance to play and see how things actually work

I've just gone with hosted exchange through ihostexchange.net

No worries.

Its a standard stupid mail trick to do rewriting, though its somewhat frowned upon. I've had my domain and mail account for over a decade now and I don't ever want to change it.

mail2web.com has been mentioned on the other thread regarding push email, and it is what I use.

I have it setup for my own domain, and gives me an Exchange 2007 server to run contacts, calendar and mail through, linked up with my outlook account. I can also use the web version of outlook through the exchange server's website.

Well worth considering if you'd like an Exchange server, with support for your own domain.