Friday, August 8, 2008

Gmail and Multiple E-mail Accounts: the New Definitive Post for the Best Way to Set Up a Single Log-in E-mail Solution

what's playing: "Still" by Ben Folds

A while back I created a post called "The Definitive Thunderbird - Gmail Set Up For Retrieving From Multiple E-mail Accounts." Since then I've realized that Thunderbird is not the answer (for me).

My goal is to be able to keep tabs on my 20+ e-mail accounts (I know, a lot, but I have many different entities and business ventures that I like to keep separate) from anywhere there is a computer for me to use. I thought Thunderbird Portable was going to be the answer, but after using it from a thumb drive for several weeks, the speed limitations took their toll upon my patience. I was monitoring too many e-mails and downloading too much material for that system to be efficient. It may be something that works for you, especially if you don't have a slew of e-mail aliases, but for me, it was no good.

It might also work for you if you aren't actually downloading your messages (using IMAP or whatnot), but for me, I then ask, why use dedicated e-mail software at all? Why not just use web mail so you've got it wherever you are?

I also tried switching Thunderbird Portable to my system hard drive to speed things up; then I would copy my Thunderbird Portable folder to a thumb drive only when I traveled, but I still ran into the same problems (sticky and slow) when I was away from home.

So I'm back to just Gmail. And I'm setting up most of my clients with similar setups, tweaked to their specific needs (see an example after the "gripes").

First, my gripes with Gmail:
  1. They look at your stuff.
    Granted, they claim elves and monkeys are the only ones scanning your private messages, and they're doing it "only" so the little adds (you barely notice them) in your Gmail interface are targeted specifically at things that matter to you (what's in your e-mails). Still, I'm not thrilled about anyone or anything going through my personal communications.

  2. There's no whitelist.*
    After literally YEARS of griping about this (I wonder how many times I wrote in to "suggest" this), Gmail finally implemented "Never send it to Spam" to their weak list of filter options. So now, you can set up a filter using "has the words," enter a domain name, and check "Never Send it to Spam."

    It's about freaking time, Google.

    *settings>filters>create a new filter>(fill in info)>(check "Never send it to Spam")

  3. The Spam filter is too voracious.
    The effects of this have been somewhat minimized by the new "Never send it to Spam" option, but I still find myself having to go through my spam box to find e-mails that people claim they've sent me. It sucks when someone contacts you for the first time about wanting to cut you a record deal or having you build them a $10,000 website, only to have their offer or inquiry go straight to spam.

    All my social networking notifications used to go straight to spam, so I wasn't getting clued in when I had 10 new Event Invitations from MollyMcCheesie or when 84 people had sent me Instant Karma on Facebook. Gmail seems to have laxed (did you know that technically "lax" can't be used as a verb?) some of their kung-fu grip on these notifications, but you can also just set up a "Never send it to Spam" filter with a portion of the "from" address for notifications from these sites.

    The other group that so often goes into the spam box, is in fact, mail sent to groups. If you're on a list, chances are the mail is in your spam box. This is OK if it's a list you receive from regularly, once again, just set up the "Never send it to Spam" with the people's addresses who are also on the list. But when someone decides to have a cookout and puts your name in amongst others on a list that has never existed before... chances are it's going into your spam box.

  4. The damn "sent on behalf of."*
    If you use Gmail as a catch all, your central depository for all your mail to route to, any time you send from there, the recipient can see "sent on behalf of." This might not sound like that big a deal, but if you're trying to broker a deal with Sun Trust Bank and you think you're sending from your "" address and instead the President of the company receives mail from ""... it's just not cool.

    Yes you can set up multiple accounts to use from within Gmail, but everything is still "sent on behalf of" your Gmail account. This is especially true when people are receiving your mail with Microsoft Outlook, which most business suits are.

    *Google Apps is the best workaround at this point. You can set your MX servers for your domain to use Gmail instead of your own server, thus mail is actually being sent from your domain address, instead of "on behalf of." If you're still using one central account, you'll still be using aliases, but I think setting up a domain with your name is the best solution here. That way, mail sent from aliases are sent "on behalf of", so there's nothing really suspect or weird about that. Also note, unlike a regular Gmail account, you can be logged into multiple Google Apps accounts at once (no logging in and out to send from each account).

  5. At any given point, you may lose all your messages.*
    About nine years ago, before Gmail even existed, I was using Hotmail. At the time I had just started dating the most wonderful girl on the planet. She is now my wife (woo-hoo!). I was corresponding with here incessantly via e-mail. I planned on printing up all those e-mails and binding them into a book of our correspondence (awwwww...), but before I could, Microsoft pulled the plug on the account for no apparent reason. Wham. Vanished. No hope of ever getting any of it back. I've hated Microsoft ever since.

    *The simple solution to this is simply backing up your e-mail every now and then by using Gmail's Pop Mailbox function to download with any number of e-mail applications. Lesson learned.

    [August 12, 2008, update: It wasn't losing everything, but many, many Gmail users reported not being able to access their accounts for hours yesterday. I don't know if it was related, but one of my accounts' passwords had to be reset. Just saying... Gmail is not without fault.]
So, on to an examples of what will work...

In a nutshell, this example shows how to have all your e-mail download to your computer, while also making all e-mail available on your central Gmail account (without using IMAP, which is another solution you could use).

The client has a main domain (e-mail and website hosting), an alias domain which he uses just for his "secret" e-mail communication, and a Gmail account for when he doesn't have his laptop with him. He definitely prefers using his MacBook Pro (with Entourage) and it's important to have all his e-mail messages actually on his laptop. He travels a lot and is often in remote locations with no Wi-Fi, and he needs to still be able to access the information in his e-mails.

The important thing with creating his setup was to make sure any e-mail downloaded directly to his laptop was also accessible via his Gmail account (for when he only had access to someone else's computer, and not his own). If you're setting up a central Gmail account, I think it's important that you be able to access all your e-mail there, as well as on your personal computer.

The solution: (downloads with Entourage; forwards to Gmail) (only forwards to (only forwards to (only forwards to (only forwards to (forwards to (only downloads with Entourage)

There are two main "tricks" with this setup.

One is to set up the (the Gmail catcher) and the other is to set up a filter on the Gmail account which states "to: forwards to". This way, only mail addressed directly to the Gmail account will forward to the Gmail catcher. This is important so that you don't set up a loop that will cause an e-mail to continually forward back and forth from Gmail to the main account.

Obviously you still have the problem of the "sent on behalf of" discussed in #4 above. Again, the best way around this is to use Google Apps so that the Gmail account is actually an address with your name (see #4 above), or resign yourself to the fact that people will see your Gmail address, and just don't make the address too dorky.

The other issue you'll need to address is having a copy of your "sent" mail available on Gmail if you've sent from your e-mail program. The workaround to this would be to set up your e-mail program to blind copy (bcc:) your Gmail address on everything you send out from your e-mail program. You'll also need to blind copy your address to have "sent" mail created from your Gmail account available on your local machine.

Don't forget to set up your aliases in Gmail.
Settings>Accounts>Add another e-mail address... and then make sure to select "Reply from the same address the message was sent to."

There are obviously other ways to set this sort of thing up with your specific needs. The important part is to avoid creating loops, and the cleanest way to do this is to set up the filter on your Gmail account that forwards mail addressed directly to the Gmail account (not forwarded there) to an account on your server that is used only for catching Gmail (not forwarded anywhere else).

If you don't need "local copies" and aren't concerned with Gmail's overzealous spam filters (don't forget to archive though), your setup is much simpler. All your e-mail accounts should just forward to your Gmail account (make sure they delete from your server or you'll clog up your system), and then you can download using Pop from Gmail.

For those of you asking: "Why not just have everything forward to Gmail and download via Pop from there," I point out again Gmail's crazy spam filter. If you're only Pop-downloading from Gmail, chances are you're missing e-mail that's been erroneously directed to your spam box.

Hope this helps anyone looking for a good, solid, single log-in e-mail solution.

Leave a comment with questions if you have any.

Don't forget to listen to (or better yet, buy) some music while you're here.



ksg said...

For a solution to the "On behalf of" problem, see the discussion in David Pogue's NY Times column of a week or so ago:

The Invisible said...

Thanks for checking in, KSG, but I don't really consider LaoPowerTools a solution as it leaves Vista users out in the cold (for now), and it only works with Mac Mail and Microsoft Outlook.

Also, the minimal info I can find on the company would make me very nervous about using it for any sensitive communication.

Perhaps I'm overlooking another solution in the 60+ comments on that post, but #38 is the only one I see addressing the "on behalf of" issue, and it states simply (paraphrasing): use LaoPowerTools --and that guy/girls only been using it a week).

Anonymous said...

why yes I am aware that "lax" isn't to be used as a verb, thank you very much.


Anonymous said...

google apps is a good alternative, however there are some features missing in google apps docs as compared with regular google docs

another trick is to use a firefox plugin like gmail manager, if you can find some way to sync your browser

the only true way to login to multiple gmail or google accounts is to use multiple profiles

this can be done in firefox 3 with "firefox --no-remote -ProfileManager"
(this may vary a bit by operating system)

it can be more trouble than its worth however, and this is an ongoing issue that needs more attention :)

another alternative is some websites offering multiple login to multiple webmail services, is the only current one i know but its not 100% perfect, anyone know of similar alternatives? in the end that is probably the most usable kind of method

Anonymous said...

Thanks for experimenting with this and sharing your experience and set up. I work in two states and am constantly on different computers with email access being a high priority.

Like yourself, I have a number (not as high however ;)) of addresses that I respond to from working with several companies. I would love to use gmail if only for the 99% uptime web access and a great labeling system. I do not own a tin foil hat and have nothing to hide and have actually found great companies by clicking on the robotically placed ads.

I also started using thunderbird portable about 2 weeks ago and cannot stand the lag (thanks for the hard drive tip...duh!). The kicker came when the other day I misplaced my drive - quickly realized how flawed my original "all my eggs in one basket" idea was.

The fact that Gmail has to ad the sender field with your gmail address is a total deal-breaker however. Personally, I think it is one, very unprofessional and two, a very good way to put my email address in the wild for spammers to pick up. I'm curious if you are just taking the good with the bad here and biting the bullet.

Anyway, I believe I found my solution which I am going to try this weekend. I plan to have my gmail account pull all my pop mail using the mail fetcher and remove it from the respective servers. Then I am going to set up TB Portable to pull my gmail using imap instead of pop. There is a great resource explaining the benefits here which essentially outlined the reasons why I decided to go this route - labels included!

Hopefully you will find this interesting and thanks again.

The Invisible said...

Goolooger- if I were going the route I think I'd just use Thunderbird portable with IMAP pulling from a central Google account.

Bawlmer- as stated above, the IMAP route is likely where I'll end up, though I'll be playing a little bit with everything funneling into a central Gmail account vs. pulling from several accounts. The obvious upside to the central account is all your e-mail in one place online if you don't have your thumbdrive and portable TB with you.

IMAP seems to be the answer.