Check List for Email

I am amazed at how many people are using email that is broken. Yes they get their messages, but they have to jump through all kinds of hoops to make things work right. Worse, many people have setups that are actively exposing their passwords to anyone who cares to look.

Here is a checklist of essential items for an email provider. How does your solution rate?

1. Webmail and Mail Client Synchronized
2. Ability to Send from any Connection
3. No Plain Text Passwords
4. Secure Connection
5. Backups
6. Adequate Storage Size
7. Anti-Spam
8. Anti-Virus
9. Aliases
10. Mobile Connections
11. Strict Terms of Service

Now lets look at each of these items in a little more detail, because some of them aren’t necessarily intuitive from the one line description.

1. Webmail and Mail Client Synchronized

This is something that I see a lot of people just assume isn’t possible. When you log into webmail and delete a message it should delete it from your email client as well. When you delete a message from your email client, it should delete it from webmail. If you open an email on your desktop computer, it should show up as read on your laptop and webmail.

Generally, the only way to do this is by using IMAP. If you try to use POP3, you lose this capability.

The synchronization can go well beyond just the inbox. Ideally you should have a synced copy of all your contacts and calendar items from any device. If you log into the web client and add an appointment it should show up on your desktop and your laptop. If you add a contact to your Blackberry, it should show up automatically on your webmail client.

2. Ability to Send from any Connection

Many service providers are attempting to combat viruses and spam by blocking outgoing email. For example, if you have a Comcast connection and try to send email using the Comcast server, it will work, but if you try to use a server other than Comcast, they will block your message.

I see a lot of people just put up with this. They just learn to cope with the idea that they can send mail from some places and not from others. If you have a good mail provider, you shouldn’t have to deal with this. Most good email services will give you an alternative port to use–one that isn’t being blocked. That way you can send email regardless of whether or not you are on your home network, the airport or at a friend’s using their connection.

3. No Plain Text Passwords

When your email client checks email, it has to send a password to the server. There are several ways to do this, but the easiest is usually to just send it as plain text. This means your password is sent in a way that someone sitting in Starbucks next to you can pull it out of the air if they want to.

Your email solution should be configured to not allow plain text passwords. That way when people are setting up their computer they can’t accidentally choose the unsecure option.

It is safe to use a plain text password if the connection you are sending the password over is encrypted, which brings us to our next point

4. Secure Connection

Some systems encrypt the password, but then transmit the contents of their email back and forth in a way that anyone can read it. You want your email setup to do IMAP and SMTP over SSL in order to prevent this. If properly configured, your password will use this encryption method as well.

Not only do you want a system that supports a secure connection, you really need one that requires it. If someone sets up their own laptop to check email, you don’t want to have to rely on them understanding how to set up a secure connection. If they don’t set it up securely, it shouldn’t work.

5. Backups

If you accidentally delete your entire mailbox from your computer and from the server, you need to have some type of way to get it back. Having a local backup using Time Machine or another backup program is important, but ideally there should be a server-side backup of the server files that goes back at least a few days.

6. Adequate Storage Size

If you set your email up correctly using IMAP, all of your messages will stay on the server. This means you need to make sure you have enough space to store everything that might be in your mailbox at a given time. If you empty your mailbox completely on a regular basis, this probably isn’t a big deal. However, if you are like me and like to keep a record of everything you’ve sent or received, you’ll want to make sure you have a good amount of storage and that you have room to grow.

In general, emails take up very little space. A 1 Gig mailbox will take a very long time to fill up with emails. Attachments, on the other hand, are a different story. I keep my mailbox under control by moving anything with an attachment over a few megs to my file system.

7. Anti-Spam

I see a lot of people relying on anti-spam software on their PC. Most spam should really be stopped on the server, not on your computer. If the server can stop a good portion of spam and only allow through good messages or messages that are hard to determine, you can use your local anti-spam measures much more effectively.

You also need to consider what happens to emails that the server flags as spam. Sometimes it is ok to delete these directly. Messages from domains that don’t exist or that are obviously malicious can be dropped at the server. However, the other messages need to be somewhere accessible–just in case something gets tagged as spam incorrectly.

With IMAP, you should be able to keep a folder called SPAM and have the server put anything that it thinks is spam, but isn’t 100% sure, into that folder. That way, if you are expecting an important email that doesn’t come when expected, you can easily check the folder to see if it was flagged as spam.

8. Anti-Virus

Like spam, it is better to catch a virus on the server before it makes it to your inbox. This doesn’t mean you don’t need to have some type of anti-virus on your computer, but if a big virus breaks out, the server can take quite a bit of the load off your local machine.

9. Aliases

This is the ability to have more than one email address to receive mail. For example, I may have an address of [email protected] and an alias of [email protected]. Any messages sent to [email protected] go directly into my [email protected] mailbox.

Aliases allow you to create an email address for a particular role in a way that is easy to move around if the role gets assigned to someone else. So when I start my company [email protected] may come to me, but when we get an accountant I can switch it to their email account. If I just used [email protected] I’d have to forward a bunch of messages while we changed all of our printed material to show the new accountant’s email address.

Aliases also allow you to create a disposable email address if you need to sign up with someone you don’t trust not to spam you.

10. Mobile Connections

Your email solution should allow mobile connections. For example, if you get stuck in an airport without a computer, you should be able to use the browser on your phone to look at your emails and maybe look up a phone number in your webmail contacts.

Most webmail interfaces are setup for a desktop and won’t work on a mobile device unless there is another version of the interface specifically designed for mobile devices.

11. Strict Terms of Service

This might seem unintuitive, but you want your email hosted somewhere that has a strict terms of service. If you try to send an email out to 500 people all at once, it should stop you. Providers who are serious about not showing up on blacklists have to be very strict with what they allow their clients to do. If they aren’t strict, they will attract spammers and their servers will eventually get blacklisted, which means your emails will have a more difficult time going through.