[Discuss] small business and "prosumer" email options: Yahoo Business Email, FastMail

[Tom Metro]

[Reposting from BBLISA, as this may be of interest to BLU readers.]

Back in May John Miller asked[1]:
> What's everyone running for spam filtering these days?

which led to a discussion about practical email setups for small
business and power users, which led to discussion of the pros and cons
of Gmail.

Since then I've ran across a few things. One is that Marissa Mayer seems
to be trying to make Yahoo! Mail competitive with her former employer,
Google, and they now support IMAP for free[2]. Apparently they'll even
host your own domain for $35/year[3] with unlimited storage (that
includes some limited web hosting as well). (Oddly all their marketing
aimed at business only promotes POP, with no mention of IMAP.)

Given Yahoo is the creator of DomainKeys, as you'd expect their service
includes generating DomainKeys for outbound mail, and presumably using
it to filter inbound mail. (Though many other providers will as well.)

No evidence they support address extensions. They also charge for
aliases the same as mailboxes[4]. So that $35/year account that supports
only one mailbox is unlikely to satisfy a power user or even the tiniest
of businesses.

Interesting that they're trying to be more competitive, but they have a
long way to go before I'd seriously consider trusting my or a client's
email to Yahoo.

> 1. http://www.mail-archive.com/bblisa@bblisa.org/msg04316.html
> 2. http://help.yahoo.com/kb/index?page=content&y=PROD_MAIL_MOBILE&locale=en_US&id=SLN3361
> (With current versions of Thunderbird, the account setup wizard, when
> given an @yahoo.com email address, will automatically use the correct
> Yahoo server settings for IMAP.)
> 
> 3. http://smallbusiness.yahoo.com/email/
> 4. http://help.yahoo.com/l/us/yahoo/smallbusiness/bizmail/forwards/forwards-08.html


I also ran across this blog posting on "Switching from Gmail to
FastMail"[5]. What's FastMail[6]? I had never heard of it. Apparently it
is a hosted email service ran by Opera Software (yes, the browser guys)
that actually predates Gmail. I don't think they have a free tier, only
a free trial. Personal plans start at $5/year. Business plans[7] start
at $30/year and increment by $15/year for each additional user.

Some ways in which it differentiates from Gmail: no ads, less quirky
IMAP implementation, and "personalized" support. On the other hand,
storage is not unlimited. You only get 250 MB per basic account, and
you'll pay much more per user ($30, $60) for higher tier plans with more
per-user storage, or have to buy storage at $2.50/month per GB.

They support aliases, but limit the quantity, from none on the lowest
end tier to 200 at the high end. (See the "Allowed alias quantity"
section at the bottom of [8]. None of the tier names match their current
product names, so I'm not sure what maps to what. It links to what
appears to be an obsolete plan comparison chart. My guess is that the
basic business plan includes 100 or 200 aliases.)

Of interest to power users, it also supports Sieve[9] mail filtering
rules. This is an open standard rule format, and some mail clients
provide editors to let you easily modify them. In theory, they might
also be somewhat portable, if you migrated to a different mail hosting
provider, so you don't have to start over from scratch with your
filtering rules.

But even better, FastMail supports address extensions[10], and
Qmail-style automatic mapping of extensions to folders (with automatic
fallback to parent folders; a "." used to designate subfolders). So with
a little bit of training, less technical users can make use of
sender-specific addresses and automatic sorting into folders without
writing any filtering rules.

They also acknowledges the limitations of extensions:

  The main downside of this approach is that addresses with '+' are
  considered (incorrectly) by many forms on the internet to be invalid.

Hurray that a mail provider finally acknowledges this! But it then begs
the question, *why*, if they knew this, did they stick with the
problematic "+" character. Why not simply learn from Qmail and use "-"
consistently as the extension separator and subfolder separator? (This
was perhaps the single best feature of Qmail. Fortunately, it can be
emulated with Postfix and a MySQL stored procedure.)

They act like this isn't simply an easily changed configuration
parameter. My only guess is that they came to this realization only
after rolling out the service and having customers already committed to
using addresses with "+ in them. (Plausible, if the service predates
Gmail. Though some of us we well aware of the problem before Gmail existed.)

Their solution to this problem is to use a per-account subdomains as a
hack, much like Ned Harvey suggested[11]. So instead of the normal
username+foldername at fastmail.fm format, they use
foldername at username.fastmail.fm. The two formats are interchangeable,
and presumably the latter gets rewritten to the former by some rule in
their MTA. It also implies that this requires a wildcard MX or
per-account MX records.

Theoretically, this same technique might be usable at some web hosting
providers to make their bundled email solution provide "+"-free address
extensions. But it requires a service with fairly powerful filtering
rules, a catch-all account, and some gymnastics akin to Theo Van
Dinter's Gmail hack[12].

I can't say I'm a big fan of this approach. It takes a problem stemming
from lazy web programmers and makes it spill over from an address map
rule that should be hidden inside an MTA into a collection of settings
that span MTA and DNS. Just go the extra mile and do it right by using a
different separator character.

I'm not rushing to migrate any accounts to FastMail, but the feature set
and more power-user friendly approach does sound appealing.

 -Tom

> 5. http://www.maxmasnick.com/2013/07/19/fastmail/
> 6. https://www.fastmail.fm/
> 7. https://www.fastmail.fm/signup/business.html (plan comparison chart)
> 8. https://www.fastmail.fm/help/features_aliases.html
> 9. http://en.wikipedia.org/wiki/Sieve_%28mail_filtering_language%29
> 10. https://www.fastmail.fm/help/features_plus_addressing_and_subdomain_addressing.html
> 11. http://www.mail-archive.com/bblisa@bblisa.org/msg04326.html
> 12. http://www.mail-archive.com/bblisa@bblisa.org/msg04344.html

-- 
Tom Metro
Venture Logic, Newton, MA, USA
"Enterprise solutions through open source."
Professional Profile: http://tmetro.venturelogic.com/