The Great Gmail Import & My Short Life With Web-Based Mail

About two weeks ago, I dived in to merge two years worth of mail from one
Gmail account to my existing Google Apps
mail account. I wanted to cover how it went and how it caused me inadvertently
to abandon my cherished desktop client, Outlook, for two weeks. No, it didn’t
make me a web-based email convert. But perhaps it might down the line.

Merging Gmail & Google Apps
Mail Accounts is my previous post covering some of the discoveries I made
when combining the two accounts. I had no idea it would ultimately take 12 days
to complete. During that time, I had to shift to using only web mail because any
attempt to download only "new" mail caused hundreds — thousands! — of imported
messages to be seen as new by Outlook.

Coincidentally, the Gmail blog just posted

Tips for importing old email to Gmail noting, "It might take a while for
Gmail to fetch everything from your old account…." Indeed, 12 days? I know, I
had over two years worth of mail. But both accounts are hosted by Google. There
should be a much easier, efficient way to combine two accounts without having to
go through POP downloads.

I covered some of the glitches already, but here are some additional ones:

Watch spam carefully! All new mail brought in is reassessed through
Gmail’s spam filters. This is kind of odd. If you didn’t tag it as spam the
first time, why reevaluate it and risk false positives?

Surely there wouldn’t be many false positives. After all, I
extensively tested Gmail spam
filtering when I switched over to it back in 2006. Part of the reason I
moved was that false positives were minor. These days, when I get several
hundred spam messages per day, I routinely hit that "Delete all spam messages
now" link to wipe out thousands of spam mail without a second glance. I trust
Gmail that much.

Don’t. Don’t trust it that much with imported email. I found it was nabbing
hundreds of messages that I myself sent as spam, stuff that by no means was. I
found many other important messages from others being nabbed by the filters. I
wish I’d more closely reviewed the spam messages earlier as they came in. I only
realized so many false positives were happening about midway through the
process.

FYI, of the 90,000 messages I imported, it looks like about 20,000 of them
were indeed spam that didn’t get caught the first time they were seen by Gmail.
So there is a plus to the second run in spam filtering. But it has its
downsides.

As part of this, I found myself amazed again that over two years since
I last complained about it,
you apparently still cannot whitelist people in Gmail. Insane. C’mon, Gmail, get
with it. How hard is it to allow people to create whilelists for mail that
shouldn’t be filtered. Did I miss this somewhere? And how about an option to
simply filter out any email in non-Latin languages. Trust me — anything sent to
me in Chinese is spam or something I don’t need to see. I don’t speak Chinese.
Let me filter it out. You know, like I
asked for two years ago. And
still no ability to see more
than 100 items at a time? Sigh.

The mail that won’t die. For some reason, I had about 300 messages
that refused to be archived or go away. I ended up downloading them to Outlook
yet they continued to stay on the server as if they were new. Well, 300 messages
out of 90,000 imported ain’t bad. Ultimately, I deleted them. It was the only
way forward.

Moving on, I wanted to talk a bit about using web-based email. It’s weird to
me, OK? I live in Outlook. Like if you don’t email me so that it reached
Outlook, you don’t exist. I do everything through Outlook in terms of my
scheduling, action items and so on. FYI, if you send me Facebook mail, there’s a
very good chance I’ll never, ever get back to you. Hey, I’m swamped with regular
email. Facebook mail is like a second disaster zone for me. Send me real email!
But you know, don’t. Nah, it’s OK, — I’m actually pretty good at managing a
heavy email load. Expect a future post later.

So I know people who swear by web-based email, seem to fly along with it just
fine, and more power to them. But for me, it just felt strange. Suddenly, I
found myself stuck in the world of web-based email, since it was impossible to
download into Outlook. How’d I like it?

Better than I thought. OK, it was kind of nice being able to archive
messages, assign multiple labels to them instead of having them exist in only
one folder and so on. I did get used to it.

Give me offline functionality! Still, I’m not a convert. Most
important, I need my email portable. I just did an eleven hour flight. I had 25
messages in my Gmail inbox. I couldn’t get them into Outlook. I couldn’t access
them on the plane. And the fast save I did of a few messages in HTML turned out
to not save anything at all. No offline email, no conversion for me. End of
story.

Yes, lots of Google products are going to offline functionality. But Google
Gears doesn’t seem to have given that to Gmail yet. Way back, there

was a mention that you could read your most recent Gmail messages using
Google Gears, but I haven’t played with that nor seen many talking about it as a
serious way to use Gmail offline.

IMAP’s Kind Of Cool. I’ve used POP to get my email for years. When
Gmail announced IMAP support, well, yawn. I didn’t get it. Just before I started
the merge process, I enabled IMAP thinking it was time to grow up. Instead, I
freaked out. I had all these folders I didn’t understand, each corresponding I
learned later to a label on the server. I hit the root folder out of habit and
was told it wasn’t accessible. Overall, things just didn’t feel right. I went
back to POP.

Tonight, I really need to get those 30 or so messages in my Inbox in Gmail
into Outlook. Another flight, you see — this time a 16 hour jump from LA to
Sydney tomorrow for SMX Sydney.
The problem is, after the mega import, Outlook won’t download them through POP.
It thinks they’ve already been downloaded. Time to see if this whole IMAP two
way thing works.

Cool, it did! Enabling it let me get those messages that were trapped on the
server. But the problem it, it also wants to bring over all the messages
associated with them in a conversation. Hey, I don’t need all those other
messages, and bringing them explodes my nice neat Inbox from 30 messages to over
100. Argh!

Meanwhile, I added a number of labels as part of the import process I went
through. One was called ME NOT SPAM, to list any email sent from myself in my
old account. There’s nearly 3,000 messages tagged like this in Gmail. And now I
have a folder matching it in Outlook. And if I dare click on that folder,
Outlook tries to download all of them. Gads, imagine what that will do to my PST
file.

Overall, I kind of like what IMAP in Gmail might offer. I can learn to avoid
clicking on labels that will bring up too many messages. And having labels that
can correspond to the Outlook folders I use might be kind of nice. Plus, it
offers a way to potentially get around the offline problem. But for now, I’m
going back to POP. You know, the email POP, not POP goes my heart (Music &
Lyrics, great movie, check out the clip below!)

NO BACKUP!  I realized that over the past two weeks, I have no
offline copy of what I’ve sent using Gmail. I’ve heard the rare horror story of
someone that lost their hosted data (video, pictures, email, whatever). I’ve
never worried much about such stories because I always have an offline copy of
my data, most especially email. But for the first time, some of my email only
resides with Google’s servers. Long may they wave. But the ability to download
and backup on a regular basis is vital.