Social media is a fantastic way to raise brand awareness or to promote directly to fans, but it’s also a whole new way to make you and your company look foolish in a matter of seconds. You’d think after all these years companies would have learned some etiquette, but 2016 was rife with unfortunate tweets and posts all around. Here are 12 of the biggest social media fails of the year; we hope you enjoy it more than those who posted them.

1. Microsoft’s AI Chatbot Gets Turned Into a Hitler-Loving Racist in Less Than 24 Hours

Ah, humanity. Microsoft introduced us to a kind of artificial intelligence that could adapt and learn language from interactions. Within hours, it was transformed into a complete monster spouting out horrible tweets about the Holocaust never happening, George Bush being behind 9/11 and several tweets featuring the N word and racial slurs. The project was taken down by Microsoft within 24 hours, but you can still check out some of the bot’s worst tweets.

2. KFC Australia Posts A Bizarre Sexual Ad, for Some Reason

There are a lot of ways KFC could promote their hot and spicy chicken products down under, but posting a pixelated image to look like a porn scene certainly seems like an odd approach. (What part of Kentucky Fried Chicken evokes any sort of sexual urges anyway?) KFC Australia removed the tweet and stated that it wasn’t meant to be offensive. But imagine how many people had to approve this campaign before it went public.

3. Scott Disick Blindly Uses Copy and Paste for an Instagram Caption

How hard is it to read two sentences before posting them onto the internet? For Scott Disick, it’s apparently a lot to ask. The Keeping Up with the Kardashians star-turned-DJ (lol) allegedly makes between $15,000-$20,000 per sponsored post, but he can’t take the time to read the caption before posting it. He included the instructions from whomever wrote the caption for him because writing even 12 words about a protein shake is way too much work for him.

4. The Oakland A’s and Smash Mouth Get Into a Twitter War
Who would’ve thought the most vicious and hilarious Twitter battle of 2016 would be between the Oakland A’s social media manager and band-of-yesteryear Smash Mouth? It all started when Smash Mouth tweeted their approval of outfielder Covelli Loyce “Coco” Crisp leaving the team for the Cleveland Indians. From there, things got ugly. At one point, Oakland pitcher Sean Doolittle tried to diffuse the situation with a little humor, but the two sides completely ignored him and kept throwing out absolutely lethal tweets at one another. Here’s the full interaction

5. Total Beauty Mistakes Whoopi Goldberg for Oprah Winfrey

I’m the first to give a social media manager the benefit of the doubt over an erroneous tweet, but this one is truly unbelievable. Total Beauty was live-tweeting the Oscars when they posted this hilariously bad tweet about “Oprah’s” tattoos. The problem is that it’s clearly not Oprah. That’s Whoopi Goldberg. Total Beauty deleted the tweet and apologized, but screenshots of the tweet will live on in infamy.

6. Knicks’ Coach Kurt Rambis Doesn’t Seem to Realize Twitter is Public
Kurt Rambis doesn’t have time to browse the internet for pornography. He needs it delivered to his Twitter feed on a daily basis. In February his followers noticed that he had clicked like on a very NSFW tweet and was following an account called “Great Ass Daily.” Instead of just admitting his mistake, the Knicks released a statement saying that Rambis was hacked. You know, because hackers love to break into an account, not post anything and favorite a single tweet. That’s totally believable.

7. MTV Australia Gets Incredibly Racist During the Golden Globes

Live-tweeting an awards show can get your brand a lot of attention, but not always in a good way. MTV Australia learned that lesson when they posted this shockingly offensive tweet about Eva Longoria and America Ferrera during their presentation. They soon deleted the tweet and decided to give up on live tweeting jokes about the show. That’s a great decision, just a little too late, unfortunately.

8. Texas Mattress Company Posts a Commercial For a 9/11 Sale

Technically Miracle Mattress aired their insanely offensive commercial on local television, but social media certainly helped spark the outrage over it. The Texas company decided, for some absolutely insane reason, that having a September 11th sale would be good for business. The commercial even featured two of the employees tumbling over side by side. As a complete shock to literally no one, there was a huge backlash and the store closed down indefinitely.

9. Draymond Green Gets NSFW on Snapchat

Snapchat is a slippery slope. It does give you the ability to send a photo that expires in a few seconds and alerts you if someone takes a screenshot, but it’s also way too easy to accidentally send that private photo to every single person that follows your account. That’s the lesson NBA star Draymond Green learned in July when he accidentally sent out a picture of his penis to the world. At first he claimed he was hacked, which is the most predictable and uninspired excuse every celebrity uses when they mess up on social media, but soon after he came clean and admitted he just hit the wrong button.

10. The Capitals Make a Very Incorrect Faceswap Assumption

They doubled down and responded by saying that it was a joke, but what exactly is the joke in suggesting two people have swapped faces when you know it’s just their normal faces? Good one? During the Washington Capitals’ social media night, which seems like a terrible idea anyway, the posted a tweet praising two of their fans for a “great faceswap.” Unfortunately, as they soon found out, it wasn’t a faceswap and was just a girl posing with her father.

11. Capitalizing on David Bowie’s Death

The world was left in shock with the passing of the iconic David Bowie, so companies all over the world decided to pay their respects by tying in their completely unrelated products with the music legend. Some of the more ridiculous promotions included donut holes, a shoe sale, and a wine company that didn’t even attempt to make it sound tasteful and basically just said, “Hey come drink some wine and remember David Bowie.”

12. Bill Simmons Gets Owned By Cris Collinsworth In One of the Most Savage Tweets of All Time

Bill Simmons has built a career out of sports-related snark and always being willing to voice his thoughts and opinions at any time. He decided to go after Cris Collinsworth during a game between the Patriots and the Seahawks that Collinsworth was covering by tweeting “Somebody needs to gently break the news to Collinsworth that the Pats have a weak front 7 and that’s why Seattle’s o-line looks good.” Collinsworth decided to fire back with a tweet so brutal I literally had to sit down when I read it. This was days after it was announced Simmons’ HBO show was cancelled, making this the own of all owns.