I’ll say up front that none of what you’ll read below pertains to major-provider webmail users such as Gmail, Yahoo! Mail, AOL Mail, Hotmail, GMX and so on. What I’m talking about here are those that still use personal-domain-based, company-based or ISP-based addresses that have overzealous anti-spam crapola in effect.

1. Forcing proof of who you are on reply

This one fortunately doesn’t happen very often. Someone sends you email, you reply and within seconds get spit back a message that the message you sent wasn’t received, and that you have to click a link to "validate" who you are before your reply is delivered.

Oh, I don’t think so, because that’s reverse phishing as far as I’m concerned. Guess you won’t be getting my reply there, buddy.

2. Using an email alias

There was a point in internet history when using email aliases was a good spam deterrent, but in modern times it’s not necessary anymore.

Email aliases are stupid to use for the following reasons:

• They expire. Aliases are designed to be disposable and not permanent, so whatever alias(es) you’re using may one day stop working with no warning at all.
• You may filter them out, causing important mail to be missed. The more aliases you use, the more you lose track of which goes where and for what reasons, so you’ll remove them or filter them out. Then you remember you had some important mail being sent there, but oops! Now you’re not getting those messages.
• You’re better off just using a separate email account outright. If you’re that paranoid about using your email address in certain places, just use a separate address. As long as you remember to login to it once a month, it will stay "alive" indefinitely.

3. Virus scanners that inject ads into emails sent

Sometimes you’ll see a footer on mail received that states "Scanned by [insert crappy anti-virus suite here]" – even for mails that are nothing but text. That’s stupid and nobody cares.

4. OpenPGP

Many moons ago I tried Enigmail for Mozilla Thunderbird because I wanted to see what OpenPGP was all about. I quickly dumped it because no modern webmail system (except maybe Hushmail?) supports it to the best of my knowledge.

OpenPGP is not a spam-deterrent per sé but rather a method to give you the ability to send and receive digitally signed/encrypted messages. The problem is that on receive of such messages, the bulk (if not all) of the message ends up as an encrypted mess and is completely unreadable. 

Yes, OpenPGP has its place, but for the vast majority of email communications it’s simply not required, because even if you have it, the chances of your recipients having it and knowing how it works are slim to none.

Then again, if you and certain recipients you know are members of the Tin Foil Hat club, know and understand how PGP works and how to use it, then by all means, go for it.

5. "Click here to see this message"

This is another one that’s fortunately rare but it’s still out there and is a variant of #1 above. You receive a mail from a friend but on attempt to read, you’re told to click a button because the message is hosted elsewhere outside of email requiring a click to see it. Given the heightened sense of watching out for phishing emails, this is a seriously dumb thing to send to anyone.

There’s a better way to deter spam with modern email

Instead of subjecting your recipients with a bunch of anti-spam crap, the easier thing to do is to use a modern webmail provider than can auto-import messages from your old email address.

Gmail and Hotmail for example both offer the ability to download messages from other accounts via POP, and allow you to send messages as that old account besides which. This means you don’t have to tell all your friends/co-workers/relatives/etc. to start sending mail to another account. You can still use the same account, just in a different mail system with better anti-spam countermeasures that won’t annoy anyone.

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