Moving to Exchange Online

I’ve always been in a perpetual hunt for a hosted email provider that, well, just works for what I primarily need.


So this week I moved my personal and business email to Microsoft’s offering: Exchange Online.

Exchange Online

Just to get it out of the way, I have tried the following three options for email:

They all have their benefits, but this is what I was looking for:

  • Easy setup on iOS and OS X
  • Push email to my iOS devices
  • The ability to archive in OS X without the need for any hack-y stuff
  • Filters

The only service that I could reliably get to fulfill all of those requirements was Exchange Online. Atmail would have worked well too, but I could not get push email to work in iOS, so I had to scrap it.

However, I’ll go into my Google dilemma a little bit more.

Why not Google Apps?

I use Google’s services a lot and we do use Google Apps for Education at work (and I just finished setting up Google Apps for Non Profits for another project). It works great. Gmail is a decent interface for email on the web and they offer a ton of services.

However, push email over ActiveSync is no longer supported on free Google accounts and they no longer have a free tier for Google Apps. That stinks.

So, I would have gladly paid the $5/month/user for a full Google Apps for Business account but for two reasons.

  1. I already have two Google accounts (personal Gmail and work)
  2. The way Google handles archiving and labels doesn’t mesh with how I want to work with email

The second one is just a basic tenet of working with Gmail. Labels are not folders, even when you use it like one. Archiving in creates an Archive folder that you cannot easily get into, which doesn’t sit well with me (the hack-y part) and I’m not willing to use the web interface exclusively (or the iOS app either). That is just a personal preference.

It also is a minor headache for me to deal with multiple Google accounts when working with Google Groups. If you want to send email from an email address that is signed up for Google Apps, you need to be logged in and subscribe with that Google Apps account. Makes sense, but if I have three (or four if I would have gone whole-hog), then it becomes a small headache to make sure I have the proper account signed up for the proper mailing lists.

It is much easier to have a single Google account (my old Gmail account) that I then use for all of my personal Google stuff. I’ll be able to sign up my personal and business email addresses from that single Google account all without needing to log in with a different account. Nice.

I also won’t be tempted to have multiple Google Docs, sorry Drive, or Google Plus accounts around either. Less complexity is a good thing.

So I find something different.

Will I Stay?

I have no idea. Right now, for what I need, it actually costs me less per-month to go with Exchange Online than either Google Apps or Atmail Cloud (since Atmail has a $10/month minimum). If something changes in the future, I’ll move right along again.

For now, Exchange Online does what I need with the least amount of hassle. Setting up on iOS and OS X just requires my email address and password and it really just works. The autodiscover feature of Exchange is really nice.

Push email works to my iOS devices and everything is just, well, good.

For now.


You are going to have to try out many different services to find something that will work for you. I’ve been in “transition” for a long time and have finally settled on Exchange Online, but Google Apps offers a ton of cool services to go along with email and Atmail Cloud is a viable and inexpensive alternative as well.

You really need to try them out and see what will work best for you. There are options out there, it can just be a pain to choose the correct one.

I’m glad I finally found something that works for me.

8 replies on “Moving to Exchange Online”

Welcome to the Evil Empire Bob. 🙂

Let me know if you run into any questions/support issues.

As I’ve said many times, I’m not above using the best solution available regardless of who it is from.

Just happens that Microsoft had the one this time. 😉

The recent incarnations of Exchange are pretty nice. We use on-prem 2010 here at work and I like it, especially in contrast to Exchange 2003 (cringe!). The option of doing your Unified Messaging through hosted Exchange is pretty cool too. Sets a person up to even subscribe to hosted Lync so you can federate with Skype and handle all your calling, IM, voicemail, etc through hosted services.

Its a pretty cool ecosystem in the M$ world. Hopefully they’ve figured out how to eliminate the outages that plagued the Office 365 systems. Haven’t heard anything lately.

So far it has been rock solid, but I’ve only been using it for a few days.

As a mail delivery service I think I’ll like it (which is all I want). I’m hoping they update the webmail portion of it soon to the style used at, but time will tell.

Hi Bob,

I just want to confirm you’re using this with,, etc, correct? I’m thinking of making the same move myself and I want to make sure I can stick with the tools I know and like.

I am using it with right now. I keep all of my calendars in iCloud at the moment, so I am not using it, but it is setup as a normal Exchange account so I would expect it to work mostly the same.

Hi Bob,

I admittedly hadn’t heard of Microsoft’s own hosted solution until this article (I’ve tried some of the older Exchange hosts) and it seems to be the answer to my prayers. Like you I have tried just about everything and, for the last few years, have relied on multiple Google APPs accounts to manage my email leading to the same issues with tags, multiple logins, etc. On top of that I had been on a paid account for my business work which, although adequate, always seemed expensive for the offer.

Last week, after reading your post I moved to Hosted Exchange and am so far quite happy with it (until something new comes along).

Thanks for the writeup!

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