How do I move from web-based email to email on my desktop?

If you've read many of my articles on Ask Leo! you'll know that I applaud your
decision.

But I do wish it were easier to move.

1. Choose an email service

Step one is to choose a new email service, making sure that it supports
downloadable email. Typically that means that they support "POP" or
"POP3" - they'll either call that out in their feature set or it'll just be
part of their configuration information.

I've discussed selecting an email provider before in What for-pay email
providers do you recommend?. The short answer is that your ISP probably
provides you with one or more email accounts already and they're typically
POP3 accounts.

I also discourage use of free email accounts as your sole
repository for anything important. However Google's GMail supports POP3 access
which can go a long way to avoiding many of the "I've lost everything in my
account" stories I hear. If you download to your machine and use your email
program's address book, then you control what happens to your email and how
long you get to keep it even if the actual email account were to go away.

So, having selected an email provider and created a new email account that
supports POP3 access, we move on to the next step...

2. Chose an email program

To use email on your computer instead of via a web based interface, you'll
need an email program.

Outlook Express is a popular choice (aka Windows Mail in Windows Vista)
mostly because it's present on every Windows machine.

Outlook is a popular choice for business and heavy email users. It's more
than an email program; it's a complete personal information manager, or PIM. It
includes contact management tools, calendaring, notes, and more, right out of
the box. Microsoft Outlook is a part of Microsoft Office, and while it can be
purchased separately, it's not free.

An alternative that's growing in popularity, and happens to be what I'm
using today, is Thunderbird. If you're considering Outlook Express, I'd
actually recommend using Thunderbird instead. Many of the issues I hear in
regards to Outlook Express just don't happen with Thunderbird. I actually find
it more powerful, and the fact that it does not use a proprietary storage
format means that your email is stored in a way that is easily accessible by
many other programs.

Because we seem to spend so much of our time in email, what program you use
becomes a very personal choice, and people are often adamant that their email
program is by far the best and we'd be silly to consider any other. My advice
is to look into a few and see which one makes the most sense to you and fits
your needs the best.

Once you've installed and configured your email program to use your new
email provider, it's time for a step that nearly everyone misses.

3. Backup your new email

If you're planning on having your email on your desktop machine, then you're
explicitly taking responsibility for backing it up as well as archiving it
according to your preferences. That may sound onerous, but in fact it's one of
the very reasons I advocate moving away from free web-only email services - so
that you can back things up yourself.

The majority of email related problems I hear often include the words "I've
lost everything". Either the email service was the only repository for that
persons critical email and other information and it disappeared, or they
weren't backing up what was on their own machine.

Make backing up a part of your solution from the beginning.

4. Start using your new email

This is the easy part. You're configured, you're backing up, go for it!

One important part of this is to let people know you have a new email
address. Get them to start using that address, and most importantly, make sure
that any email you send comes from that new address so that replies are
automatically sent to the correct, new address.

There are services that claim to be able to forward your email automatically
for you. Most require that the old account be kept active, they simply handle
checking for mail there and then forwarding it on when it arrives at the old
address. I have no experience with these services; I've always simply handled
that manually. Seeing what arrives on the old account is a good way to see who
hasn't updated their address book yet and a good excuse to send them a gentle
reminder.

5. Move your old mail

This is the hard part.

You have a bunch of email and contact information in your old free web based
email account. What you would like to do is simply download that
information into your desktop mail program.

It's typically not that simple.

Email first: there's actually some hope here. There are some services which
give you pop3 access to your free email accounts. Unfortunately many are not
free, and all require that you divulge your login information to that old
account. They then provide a POP3 interface. Connect to it, download everything
in your mailbox, and you're done with email.

My favorite and preferred approach uses Thunderbird. The webmail extension
allows you to configure pop3 access to your web-based email accounts. Then,
like the services above, you simply download your email. (Yes, you could
continue to use your web-based email account using this extension.
Unfortunately it's technically against most of the email providers
terms of service, and therefore not officially supported by any of them. In
other words: it could break, and not get fixed for a bit.)

Contacts and address books are another matter.

I've not yet come across a reliable means of migrating your contacts from
the web-based services to another email program. Most do not support exporting
your contacts (but all support import, of course).

I've heard of occasional hacks using an instant messaging client tied to the
email account to do some form of limited export that could then be used to jump
start a new address book in another program. It's unclear how well these
solutions work.

My only solution so far is to manually re-enter your address book in your
new email program. It's painful, but the good news is that most of the email
programs you might use do support both import and export, and you'll
probably not have to suffer through this exercise again.

6. Close, delete or ignore your old mail

Which of these you actually do is kind of up to you, but almost as important
as starting to use your new account is to stop using the old one.
After a period of time, closing the account probably makes the most sense,
though for most free accounts, if you ignore it long enough it'll go away on
its own.