Spam Filters
I have a Spam Filter. It's from a company called Postini. It's a good spam filter. It stops 75%+ of my inbound mail because it is spam.
And yet, I have to delete the first 30 messages in my inbox every morning because they are spam.
God forbid you send me an email at 3am in the morning, because I may not read it because I am fast and furiously deleting the first 30 emails I get every day.
Why can't my spam filter figure out that "pen1s" is just a code word for "penis"?
Why can't my spam filter figure out that an email address that has the word "great offers" in it is spam?
Why can't my spam filter figure out that an email with the words "free money" in the first sentence is spam?
I guess I need a new spam filter but I can't be switching these things every six months.

Being a software engineer, it's a curious question why spam filters aren't better. I know it's possible. I could even do it myself, if I had time. That's the problem with being a good software engineer, there are so many problems you're tempted to solve. Maybe the people who write spam filters aren't very good software engineers. Or just want to keep us wondering.
My guess is it's like anything else. Most people do it only well enough to succeed. Spam is so pervasive that even marginally successful solutions have a market. Why pursue excellence?
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