Worst work typo/autocorrect?

This was not a typo as I was writing but...I used to do casework for a US Senator. On my first day, I accidentally inverted two of the numbers in our 800 number. I gave this number out for over two weeks until a constituent called our direct line to let me know I was giving out a number that directed people to a phone sex service.

I just read a letter that advised that "insemination would be sought from all parties." Apparently indemnification is autocorrected as insemination.

MH and a coworker are listed next to each other in my phone. CW and I were sitting next to each other at a conference and I meant to text "I love you" to MH, but I sent it to her instead. She made a terrible face and I had a case of the church giggles for like 20 minutes.

I sent an email via phone a while back referring to one of our undergraduate workers, Heather. Except my phone auto-corrected to Heavier. And unfortunately for me (and her), she's a bigger girl.

I didn't know it until my prof pointed it out - and she was CC'd on everything. So humiliating.

OOOOH. This is bad, and totally reminded me of another one. In another department here is a Filipino woman named "Salve" (pronounced "Sal-vay"). One day my coworkers and I received an email from Salve's manager explaining some changes in responsibilities in their department, and she wrote, "From now on, note that Slave will be handling this..."
Oops.

Oh these are hilarious.
I have done the Best retards before. Luckily it was to someone I had known for a while.

Ahhhh tooo funny!

OMG LOL!

My most embarrassing one was a case where it WASN'T auto-correct. I have a friend who is gay who posted a picture of what he made for dinner on Facebook. One of his neighbors posted, "That looks so good, if I weren't so tired, I would put on a pair of condoms and walk over." I posted "LOL. Autocorrect?" because I really thought he meant to say he would put on a pair of converse or something like that. Nope. Wasn't auto correct. The guy really meant to say he would throw on a pair of condoms, as in double bagging it. It kicked off a HUGE shitstorm with my friend's friends because apparently assuming nobody would walk over to someone's house for dinner with a pair of condoms on makes me homophobic. My friend did his best to defend me but it was a mess.

Seriously, gay or straight, why would ANYONE go walking through the neighborhood with a pair of condoms on?

I was going to say they are a big hit in NE WI as well. A coworker always brings them in when she goes up to her Northwoods cabin.