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

by Jeremy Schoemaker on February 26, 2009 · 77 comments

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!

full disclosure

About the author...

– who has written 2895 posts on ShoeMoney.com.

Jeremy "ShoeMoney" Schoemaker is the founder & CEO of the ShoeMoney Blog, Elite Retreat Internet Conference, & the PAR Program. In 2013 Jeremy released his #1 Amazon Best selling Autobiography titled "Nothing's Changed But My Change" - The ShoeMoney Story. Jeremy currently lives in Lincoln Nebraska with his wife and 2 daughters.

Jason recommends you check out these amazing posts:

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1 Paul B

I’ve been using Google Apps for my domains for a good year or more and once you get your head around the no folders thing everything else is top notch. They even have a very nice custom Blackberry app that works very well. You do know that they also do a free version as well don’t you?

2 Taris Janitens

I still haven’t checked them out, but good informative writeup – thanks for the heads up!

3 Your Name (required)

I love google apps. Its a wonderful service. Everyone must try it

4 Alanna

I recently came across your blog and have been reading along. I thought I would leave my first comment. I don’t know what to say except that I have enjoyed reading. Nice blog. I will keep visiting this blog very often.



5 Zomok.my

I’d say go for Google Apps too! it saved my life from setting up mail service on my server, especially when you are moving server

6 Domain Superstar

I agree. I also just recently started using Google Docs as well and it is a beautiful thing to not have to email a spreadsheet back and forth because of the collaboration features.

7 Jim McNelis

Thanks for the rundown. We setup Google Apps for businesses, but it is easy to forget what the experience can be like for those less familiar with the product.

8 Barbara Ling, Virtual Coach

I have yet to take advantage of Google apps but with my dozens of email addresses and the like…it sounds like there’s a definite benefit to it. Thanks for the headsup!


9 Jeremy Vaught

Barbara, I run Google Apps email for many of my email addresses. I’m jeremy@ on all of them, so I can easily set up multiple domains in my one free apps account, and I get all those email in one inbox. I then simply set filters to more easily see where those email are coming from, or rather, which account they are going into. I used to do with this regular email, but apps is 1000 times better at this.

10 TED @ xs bobber

I still have a hotmail account I use personally. It really sucks.. I have Gmail for my domains and business accounts and it’s like night and day compared to Hotmail..

11 STH

Just one quick reply. You should check out Mailstore (http://www.mailstore.com/en/) FREE for personal use to keep a backup of all your e-mail. It`s like an archive for all your e-mail and it makes it very easy and fast to search through alot of e-mail – and you know where you have it.

Keep up the good work

12 TED @ xs bobber

I’m not too worried about backing up my e-mail. however all my stuff on my desktop is backed up super redundant style. maybe I should think about my e-mail backup

13 Giancarlo Massaro

They offer a free version, which I use for my company. I’ve been using it for a while now and I love it. Hardly any spam, simple to organize everything with the labels too.

14 Andreas Hassellöf

We switched to Google Mail for domains about 1.5 years ago. Had pretty much the same experience as you.

However, one more thing thats a must-have to turn on is “Enable SSL” in your Domain Settings to
Automatically enforce SSL connections.

The default behavior is to only encrypt your login information, this option to encrypt everything was added rather recently.

15 david

i agree its awesome, you forgot to say you can setup the cname records so that you just have to type mail.shoemoney.com to login docs.shoemoney.com for your Google Docs…

another recent update with the labels, is that you can now label or “label & move” which takes the email out of your inbox into archive but still searchable.

16 brian ostrowiak

we have been using this type of email for quite awhile now and ive been really happy with it… thank for pointing out some tips about canned responses!

17 nick

I also use the free version. You get all the apps but don’t get telephone support.

I could be missing something because I didn’t really look to hard but I think the $50 a seat license is basically for support.

18 Jim McNelis

it’s a bit more than that. among the standout features are: no ads, 25gb email storage, postini, video, and a variety of other features.

here is a comparison:

19 Tim Miller

postini is extra on top of that 50, correct?

20 brian ostrowiak

we have been using gmail for our servers for awhile now and have had a great experience with it… especially like the very small amount of spam…

thanks for pointing out the canned response features!

21 Ari Lestariono

Have been using gmail for a year now, i think the service is improved and quality not too bad.

22 LGR

I have been using GMail for Domains for a while and often set new clients up on it. Having Google deal with the pains of running the mail server takes a headache away from me.

People always seem to hang up on folders. Ever person that I setup, the first thing they want to do it use folders. Once you get the idea that you can use label mail and find it easier with multiple labels people usually find it easier.

23 Kenney Works From Home

I’d say that’s pretty cool. Google has their way of keeping people involved in their company with apps and marketing related stuff, Yahoo has their way with social stuff like answers, news, messenger, etc..

24 Dan Nedelko

I switched over to Google Apps for our company email and even document sharing about a year ago now.

Like you I have experienced a few hiccups here and there but overall the ease of use, management and maintenance has outweighed the infrequent outages with IMAP and some minor hiccups.

I highly recommend Google Apps!

25 Shawn

Hey, I’ve switched all of my seperate email accounts over and I also switched my companie’s email over as well (small company) to the free version. Everyone loves it, plus it’s really easy to setup on on iPHONE too, you just use the GMAIL option and it sets up the IMAP properly automatically.

26 ROW

From my personal exp, I can say that label feature of Gmail is one of the best things they have provided. It just make search and sort so easy.

Other than that there is a feature whereby you can send emails through a single account. It would appear as if they are coming from other ids.

It saves a lot of time for me.

27 Jeremy

I did the same over 3+ years ago – haven’t fired up my Outlook ever since (not kidding).

I don’t know what I would do without my Gmail Private Label *I absolutely LOVE it!

Great overview Shoe – detailed and kick ass.


28 Michael Eisenberg

Gmail and all there apps are just awesome, I like ability to sync my calendar with my blackberry

29 Blog Income Report

I’m a big fan of Google Apps but I really wonder how it would cope replacing a large corporate email server, such as a company running Exchange etc.

Shoemoney 30 Anonymous

it can not

31 Mihai Secasiu

What was the reason that made you finally decide to move?

Oh and good luck for when it breaks down and there’s nothing you can do except to wait for them to fix it.

32 Chris

I’d be real reluctant to rely on google for my companies email. I’m also a little concerned with their privacy policy so we’ll continue hosting our email @ Rackspace.

33 Chris

Ha – just realized my comments are now on moderation. You’re a riot Jeremy.

34 Nicholas

I just migrated my church and my personal domain over, and it’s been great. Our church gets the “Education” edition for free, since it’s a non-profit.

35 Ari Lestariono

I think gmail will win over yahoo on the email service since they are progressing rapidly

36 Make Money Online Tips

I was just thinking the other day about how much Google apps costs. Thanks for the detailed post.

37 TED @ xs bobber

sometimes I check my e-mail way too much though. like 10 times a day..

38 ZK@Internet Marketing Blog

So at last what is your opinion about that. I heard positive and negative. But what is the conclusion.

What are their points out of 10.

39 Dean Saliba

Switching to their mail thingy was something that I was thinking about but am now worried by the recent problems they had.

40 China Travel Blog

Am I missing something? in the past when I move my email server the first thing is to change the IP and A record to the ones of new host.

41 loans

Man, I’m surprised you haven’t used Gmail before this point.

And $50 per user still has me unsold on the idea. 25 users = $1250 annually. I can get a dedicated server for less than that.

42 Jeremy Schoemaker

heh you missed the whole point ;)

43 Scott Y.

Having a dedicated server is the exact reason why I also moved from a Postfix/Dovecot setup to Google Apps for Domain a month ago. You end up spending too much time tinkering with it (or getting it to work), than spending time on things that are more beneficial.

44 Mihai Secasiu

If you know what you’re doing you will not spend too much time tinkering with it.

45 Eric

Knowing what you are doing or not is not the point, even if you know what you are doing, you still need to put some effort on your own equipment, security patches, M$ Updates, licensing, spam filters, hardware failures, etc, for small size companies putting time on anything other than your business is a waste of valuable time and that equals to $

46 401k Rollover IRA

I hope we get to that, unfortunately we’re still circa 1997 :C

47 Classifieds

Google Apps is great for company emails, its so convenient and plus its pretty cheap. Its very worth it. It makes mailing so much easier.

48 Swingers

Ok, I haven’t switched yet as we still pay for enterprise exchange service. As a 3rd party, it still puts us managing 1 less server…but the cost per year coulld be considerably cheaper.

49 MyInternetBusiness

I to use google apps for company email mainly for easy use.

50 Tyrone

Sounds good, I will surely try this out. Why not to take the advantage of a free version first :D

51 Online Affiliate Business

Yes I think cost could be cut as much as 25% per year but have not switched yet.

52 game-lady

Google apps is a nice service,I think many people can say words of praise about its opportunities.

53 game-lady

Google apps is a nice service,I think many people can say words of praise about its opportunities.

54 yolaonda

google apps is probable a good idea but be careful and remember you are dealing with google

55 Paul Myatt

I’ve written quite a bit on my site about my experiences with the official Google Email Uploader (Windows only). I found it surprisingly buggy and could only get it working with Outlook Express. I found it’s best to move emails over 500kb via IMAP before running GEU. Also, when it stops (saying that YOU stopped it!) just restart it and it will continue. There’s also a great cross-platform program to backup Gmail (standalone and Apps versions).

56 Ron

I just uploaded about 4000 email from outlook without a hitch. Thought it worked rather well. Only had one stop and just restarted it and it went on its merry way.

57 MyInternetBusiness

I have been using google apps for around a year and find they have a very good service.

58 Online Marketing Blog

One of the companies i consult for uses google aps and it works great. I love google they are always creating new tools.

59 CheapWebBanners

I just switched my company over and it was pretty straight forward… It did take 24 hours to import my emails from the exchange server I was previously using but it was worth the wait. Couple of things I wasn’t too thrilled with are:

1. I don’t like that I can’t just view messages from my inbox…

2. They limit you to only 5 pop accounts which really sucks for me big time since I have lots of other accounts. :(

Other than that I think it was a great switch. I was paying $15 extra to verizon for business email and another $45 per month to host my emails and now I’m able to cancel those and save over $500 per year.

60 Smart Boy Designs

Great thoughts regarding Gmail. I’ve had some great experiences with the system, although at the moment I’m still using Outlook 2007.

61 Martin

For those of you who have a website and signed with Google Apps, I have two questions:

1. I read that Google Apps has a limit for sending per user. Is this real? If you have set an email account that automatically sends emails in your site (for example when a User submits a form, a user contacts through a form or a user sends an article through email), what happens if all these automatic mails pass the limit?

2. How can I do if I send a newsletter twice a week to thousands of user? How do you manege this? Did you sign up with another email marketing company?

Thank you a lot!

62 Sam

I had a very similiar experience, but recommend Gmail Premium over any other Hosted Email, mainly because it has excelent spam handling. I used Windows Live Plus before, and just got tonnes of junk.

My main complaing with Gmail is the Return-Path header. As we all have multiple identities for work online, and between client companies perhaps, I don’t want someone who gets an email from my generic info@company.com to be able to see in the header my ‘real’ email address, as info@company.com may be the inbox of the secretary who deals with reading the junk, sometimes I reply to complex queries, but I don’t want to surrender my identity this way.

I can’t see why Google can set the return path to match the sending email, if delivery fails, then the owner of the sending mailbox would like to know rather than I would.

63 Google Local Searches

google apps is a sweet thing any search engine can offer. i think they do better than any other apps from yahoo and bing in the aspect of money-making.

64 Haim Chibotero

Did any one here have a list that compare gmail premium to exchange2007 features ?
I know they don’t have public folders , what else are they missing ?

is it easy to share someone mailbox and calander ?


65 Anatole Beams

Can you have general access mailboxes (group or ‘public’ mailboxes) with this setup on Googlemail?

66 Haim Chibotero

Hi guys
any answer on my previous question ?

67 BlackBerry Deals

Hi there, just passing through. You have a really good site here! Helped me actually. So thanks and all the best! PS. Do you have a Myspace page? Thanks. Jon B.

68 Cars Under 1000 Used For Cheap

i just got something in the mail about this something to look into

69 Tommy

Google Apps is a joke, no wonder its almost free. There is to much documentation going in too many directions here. Yes this is a great solution if your not migrating any data and your creating your first email entity, but if your Outlook 2010 user or Exchange user your in for a surprise. Things DONT work like you want them to, where the functionality to have two primary accounts in the same profile? Looks to me like Google Desktop Sync only allows for 1 email address to sync, what if i want to sync multiple domains on Google, can’t do it. Thats a huge black eye, tons of my clients use 2 and 3 primary accounts (not POP) in their main Outlook windows. Having to switch between profiles isn’t a time effective option.
The support for this product stinks, you can’t call Google, you have to rely on news feeds and blogs, most of which on Google never get answered. Oh and then there are the consultants that all want 1K+ to set up a few users. But wait, if its SO easy to set up then why are the consultants that help with this simple app so expensive.
All these blogs saying its easy are BS, its easy for a particular situation, but not all, and for the most part the people that need this to work with the most features are SOL.
Back to Exchange 2010 we go. What a waste of time, energy and money.

70 Delcie Mccullick

I will immediately grasp your rss feed as I can’t in finding your email subscription link or e-newsletter service. Do you have any? Kindly permit me realize so that I may just subscribe. Thanks.

71 Akter Ali

I have been using Gmail, Docs, Calendar for a couple of years and Forms recently. I am really impressed. However now I am getting offer from Google distributors to get Google Apps for my Office. There is one big question is in my mind now if anyone can answer:

If we need to switch out of Google in future what will happen to the old mails and all other data that will be deposited in Google server over the years?

72 eli

hey, thanks for this post. do you have any info/advice on migrating emails, calender and contacts from microsoft outlook web access to gmail?

73 Greg


Don’t bother. Switch to Exchange online. If you are an Outlook or OWA user you will be disappointed by all the crap you have to put up with and now Exchange online is cheaper than Google apps with much better support and if you add encryption the costs is significantly less than Google apps. Having switched my company from Google apps 1.5 years ago I’ve regretted it ever since and I’m in the process of going to Exchange online.

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