Switching To Google Apps For Your Company’s Email (My Experience)

For over 10 years now, I have either ran or had control of my own mail server. Well, at least it was that way until 2 weeks ago.

Google’s apps includes hosting premium applications (of which the biggest thing is Mail) for $50 per user per year.

I have been curious about switching for quite some time but thought the flexibility of having my own server outweighed the benefits. Well, 2 weeks ago I finally decided to make the switch.  And now I have to say that although things have been great for the most part… there are still a few quirks that frustrate me.

Like most things on my blog, I will take you through my experience in switching over. Hopefully it can help you if you decide to convert one day, too.

Step 1) The setup.

Setup is SUPER easy.

I started out by purchasing 5 accounts. At first, you have to specify 1 of the accounts as the administrator. I made the mistake of making an admin@ and using that for an administrator instead of just using my own email. (Later I figured out that I could just use my own email as the administrator.)

With Google’s really simple walk-through on what to change for your DNS, I was able to quickly make the right changes. (But if you have already run your own mail server, this should not be a big deal anyways.)

During the setup process, you can also make a catchall account. (A catchall account means that you can specify 1 user as the catch-all for anything you forgot.) I started off using Brienna’s email for that but it got so much junk that I used info@ for this instead.  Also for the Auto-Responder (out-of-office) purposes, it’s much better to have a seperate account for catch-all email rather than just using filters (which I will cover in a bit).

Step 1.5) Special NOTE

If you are an IMAP email user and do not store mail locally right now, you’ll have to remove all accounts from your desktop client. Your mail will be on your old server and you’ll have to migrate it. (But if you leave desktop clients setup, it’s going to be a clusterfuck – trust me.)

Step 2) The Migration

The administrator can setup the old mail server and then start to migrate all your folders.

*IMPORTANT* Gmail does not let you make new “folders” as you know them. They have an all mail folder which ALL MAIL goes into then things can be labeled (which will appear like folders and ACT like folders on your desktop client). All of your newly imported mail when you first import it will look like INBOX/Travel or INBOX/Sample.

Once your import is complete (it took over 24 hours for mine to fully complete), the only things you still need to do is move/delete your old sent mail and trash. (DO ALL MOVING ON GMAIL!)

Then rename your labels … instead of INBOX/Travel just rename it to Travel. Repeat this for each label.

With Gmail, the email is not stored in these “labels” – it’s just organized there. Essentially, all your mail is set in the All Mail folder. These labels will appear like folders in your desktop client later, but just know that if you delete a label, the emails with that label will not be deleted. They will still be in the all mail folder. You are just deleting the label. Also, you can have more than 1 label per email (which really makes this cool). I know, I know… some of this may seem redundant to you if you’ve used this for a while – but it took me some time to fully understand how this works. I had never used Gmail before.

Step 3) Contact Migration

Even if you are going to use a desktop client 99% of the time, it’s very handy to have all of your old contacts available. There are guides on Gmail for everything under the sun except for Apple Mail.app users. Don’t worry – there is an easy converter (like stupid easy). The application I used is called A TO G and it’s free (although donations are appreciated). I still think that dude should charge $50 for it though, because without it the process sucks…

Step 4) Client Setup

Now you have all your mail setup how you want it INSIDE Gmail and your migration is finished. (You can now delete the migrated mail label if you want –  it has just labeled all the mail that’s migrated.)

On each of your desktop computers, set up a new IMAP account with:

incoming server: imap.gmail.com (secure port)

Username: username@yourdomain.com

Outgoing (SMTP) server: smtp.gmail.com

Username: username@yourdomain.com

Password: the password for the user you’re setting up (DUH).

Step 4.5) Don’t set up all your desktops at once.

I currently have 6 different computers I could possibly check mail from.  2 laptops,  my office mac, home mac, home/office mac, and Windows PC.  I made the mistake of trying to set them all up the same day and started getting errors… it turned out I was exceeding my daily bandwidth limit (who knew?).  So instead, I setup 1 per day and since then they have all been fine.

Step 5) Don’t forget to check in on your old stuff.

Inside Gmail, go to your accounts and pop mail from old accounts or other accounts.  I setup a .forward on my old mail server for each of our users just incase something goes there.

Step 6) Setting up the cool shit.

Be sure to check out the Google Labs. I would suggest enabling the following “must have” labs:

Canned Responses – I try to answer every email I get and 95% of the time I am just repeating myself.  Canned responses have dramatically sped up my email response time.  You can also use canned responses in your filtering.  It’s kind of like an Auto-Responder/out-of-office message but only for certain people.  For instance, let’s say someone emails me through the Contact Us form and somewhere in that message the terms “paid links” or “paid review” are found.  I can then make a filter that will allow me to reply with a canned response stating that we do not sell paid links but we do occasional do paid reviews with no follow links for a particular price. And bam! Just like that I’ve answered the email. That’s nice.

Send and Archive – This is probably one of my favorite features.  It gives me a extra button inside my mail window next to the Send button. This feature allows me to both send a response and then remove the mail from my Inbox.  How many times do I really want to save something I have already responded to??  Yea, never.  Also, archiving is NOT deleting.  It’s simply putting it into the All Mail folder.

Offline – This app let’s you access your Gmail (the last sync of it) without an Internet connection.  This is pretty hot.

Reply To All Default – Setting this up makes it so the default button to reply/forward is actually “Reply To All”.  For about 99.9% of all my emails, I WANT to reply to all.  With email, I often forgot to do this so I’m loving this feature.

So … pretty big step for me.  I migrated myself and 4 other users (dillsmack is still not convinced yet). Am I glad I did it?  Well, in the beginning I was not so sure.  At first, I didn’t really get the labels idea and man… when I first saw that crap saying my bandwidth had been exceeded, I started thinking, “Oh, great!” (Thank god it hasn’t happened again.)  Other things that still bug me include:

1) Flakey connections. While checking or sending mail, occasionally I am asked for my password. (But hey, maybe it’s because I leave myself logged in on multiple boxes? Not quite sure.)

2) Return path header.  After racking my head trying to use the filter/canned response and out of office/vacation feature, I noticed it was replying NOT to the reply-to or reply email, but rather the return path header.  Dillsmack made a thread in Google groups and while this is against the RFC, it looks like Google is keeping it (as retarded as it is!).

3) IMAP Downtime. Occasionally the IMAP servers are just unavailable.  It doesn’t seem to last long and has not happened much.  Maybe it’s just been a fluke.  I can always tell I am not alone just by asking on Twitter or using Twitter search.

4) It’s also $50 a person.

Let’s look at the positives.

1) 1 less server to maintain.  This is huge IMO.  It’s one less machine we need t0

  • Maintain Hardware
  • Update spam rules
  • Update software for security
  • Administrate

2) Spam filtering – AMAZINGLY AWESOME.  I now get 1-2 spams a day.  I used to get between 20-40 a day.

3) Simple things.  Before, doing a out-of-office meant writing a special rule….  Nothing too hard but the more our business grows the simple things start to have a big expense in time and what it’s taking time away from.

4) Mobile application.  The Gmail Blackberry application is SO NICE.  In fact, I’ve given up on the default Blackberry and now this is the only one I use. Searching through folders/labels and looking up contacts is so slick. It also integrates nicely with the other applications.

5) Branding – no need to say more:

If you are thinking about switching to Google for your domain…. I say go!