successfuly upgraded my iPhone firmware to the cool new spanking 2.0.  Upgrading byitself was a journey.  It was about a 3 hour process with 4 failed attempts.  The final 5th attempt was successful and my trick was turning off my virus scanner.  Enough with my upgrade blurb, I'm here to write about my quest to get Hotmail working with the iPhone.

Here's the simple plan:

  • Step 1: Upgrade my free hotmail to Hotmail Plus 
  • Step 2: Setup my iPhone to use Hotmail Plus Pop3

Step 1 was actually harder than i thought.  It wasn't hard actually upgrading, but it took forever to find the stinkin link.  I used google to search for the link, so I'm not sure if it was google hiding it, or if microsoft did a bad job at advertising their service.  Also, when i finally got to the link it never really mentioned pop3 as a feature.  I was hearing about the pop3 via various discussion boards.  At one point someone called it the "hidden" feature.  So I took the risk and went all in with $20.

Step 2 wasn't bad either.  There were some basic settings that i'll post below.  Pretty straight forward.  I was really suprised that it took the connection settings with no problems.

Now here's where the marriage goes wrong.  I click on Mail on my iPhone -- so far so good, I see my Hotmail account listed amongst others.  I click on my hotmail account -- so far so good, I see my Inbox sitting there.  I click on Inbox -- hmmm...empty...nothing appears....wait there's a mail, there's another, here it comes...it all works great!!!  I was estatic to see the mail flowing down.  A little closer look into my e-mail then revealed that it was grabbing my e-mail starting with my earliest in '04.  Mind you i have 5000+ e-mails in my hotmail account.  Don't ask why, cause i couldn't tell you why.  So now I'm at a point where my e-mail works, but I can't really read the e-mail i want to read.  It totally bites.

I am now attempting a workaround.  My theory on what's happening is that now that mail is going through Pop3, that all the e-mail is being treated as new/unread e-mail.  So i'm thinking the iPhone is treating unread as recent?  Maybe, possibly?  I've now setup my hotmail via pop3 in Outlook and it's downloading all of my e-mail as unread.  So from here I'm going to try to mark all the e-mail as read, and see how that affects the iPhone downloading my hotmail.  I have both fingers crossed!  Worst case scenario I can use outlook to do some despratley needed cleanup and filtering.

I'll update this blog post with my results (since it's going to take hours, days, maybe weeks to download all of my e-mail).

Here's the Windows Live Pop3 settings:

Account Information:
Name: John Smith (note: enter your own name)
Address: example@hotmail.com (note: enter your full Hotmail email address)
Description: Hotmail

Incoming Mail Server:
Host Name: pop3.live.com
User Name: example@hotmail.com (note: enter your full Hotmail email address)
Password: password (note: enter your Hotmail password)

Outgoing Mail Server (SMTP):
Host Name: smtp.live.com
User Name: example@hotmail.com (note: enter your full Hotmail email address)
Password: password (note: enter your Hotmail password)

Advanced Settings:
Incoming Uses SSL: On
Outgoing Uses SSL: On
Authentication: Password
Delete from Server: When removed from Inbox (or your preferred option)

Update - Great Success!

So what I did was setup Outlook on my desktop to use Hotmail and Pop3.  It took Outlook probably a couple hours to download 5000+ e-mails, which were all downloaded as unread messages.  A side affect was that after downloading each e-mail, the e-mailwas also deleted from the server.  So if/when i login to my hotmail via a web browser, I get 0 messages.  So now when I check my iPhone I'm only getting my new messages.   That's exactly what I wanted.  I did change some e-mail account settings in outlook so that it would leave e-mails on the server for 30 days.  I also setup my iPhone so it deletes e-mails on the server when I delete from my iPhone.

Update 2

For my scenario, there are some settings which I feel work best for me.  I'm using outlook as my main e-mail app and my iphone as a secondary e-mail app.  Therefore in Outlook, I changed the accounts settings on my hotmail so that it leaves a copy of the e-mail on the server but deletes it after 10 days.  This allows my iPhone to download 10 days worth of e-mail.  I also setup my iPhone to not delete on the server, I let outlook do that work.