I’m forced to advise a Windows-based client of mine who is computer illiterate (we’re talking caps-lock messages and not knowing what a web browser is) and needs to start using email more for her home business. A good candidate for Mac, but right now that’s not happening.

She uses her web host's webmail now and it’s a huge problem. So she needs an app with basic IMAP email functions including attachments. Nothing fancy. She needs something that is easily supported—not by me, but by any Geek Squad equivalent she brings in on a given week. (So, no random open source solutions.)

Two vital features:

1. Spell check

2. Being able to have two IMAP accounts and look at them separately (not intermingled) without ever re-entering the passwords after the first time.

Since ease-of-use is more important than feature bloat, I tend to recommend Windows Live Mail... which I’ve never seen in my life. (I assume it can do both of those things?)

She already owns Office, though, so here’s the question: Is there any reason I should steer her towards Outlook instead?

Thanks in advance!

Live Mail separates the mail into separate folders.

Outlook puts all mail into one Inbox, you'd have to set up rules to separate it.

Both do IMAP, and spell check when sending, I believe you have to turn it on in both in Tools/Options, it's off by default I think.

Don't know about holding IMAP passwords for sure but they both remember POP3 passwords.

There's also Windows Mail which doesn't necessitate a Windows Live account like Live Mail, but it doesn't do separate folders, it's a slightly watered down Outlook.

I see. Good roundup of the options! Many thanks.

Separate folders are probably worth it.