@silentwish Hey there! Solo slooping is definitely the hard mode way to play Sea of Thieves. First, I recommend using the official discord or reddit discord to find people to sail with. If you don't use discord, check out the official sea of thieves xbox club.

I'm in the process of making three videos: How to solo the Kraken, how to solo skeleton ships, and how to solo the Megalodon. Currently working on the first which is the Kraken.

For the time being, here are the general tips that will be in the video. A general tip not specific to any of them is to always be supplying the boat with resources. Suck the island dry that you spawn into.You should be able to leave with ~70-80 cannonballs and 35-50 planks & bananas. Gather supplies at each island and park for floating barrels until you are well supplied. You can actually survive most of these fights using less than 15 planks if you do them right. Cannonballs will become your bottleneck resource.

Skeleton ships

1. As soon as the skeleton ship targets you, sail to the closest island. The bigger the island the better.
2. Park your sloop in shallow water as close to the island as you can by raising your sails. Make sure you are turned so that your broadside is facing the island and the other broadside is facing the sea. The skeleton ship should now be circling the island.
3. The skeletons hip will only be able to hit you when it's on your side of the island (unless it is a small island and there is no tree cover). During this window, return fire and spread your shots out across their hull. Since they can only patch holes and not bail water, you can wittle them down over time.
4. Once they are out of your firing window, repair and bail. You want to do this when you are not able to hit them with the cannons. You shouldn't have to repair the holes in the back of the sloop because they do not leak when stationary in shallow water.

Kraken

I'll quote myself from another thread:

First thing I do is raise my sails completely. She has you at a dead halt pretty much in the beginning but as you fight her your ship will move. If you somehow get off the boat this becomes a problem. It also makes it harder to hit her with the cannons because you have to factor the sideways velocity of the cannonball into your shots.

The trick is to be super aggressive against her. I noticed that in my failed attempts to solo her, I was so worried about being sucked off the boat that I didn't put out enough damage on her. You still want to avoid getting grabbed at all costs but when you are confident she is not trying grab you it is best to be firing cannonballs like a madman. Don't even bother with guns except for when she is sucking and you're hiding below deck. I've heard people say you do more damage to the top of her tentacles. No idea if that's true because I've been more aggressive in general along with shooting her near the top but she's been dying so I'm not gonna go back to shooting low anytime soon. You want to target a single tentacle at a time, try not to alternate and pick the one that is the easiest shot. If it goes underwater with out shaking back and forth it is not a dead tentacle and you want to find where it relocates. Look for one emerging from underwater shortly afterwards. If it shakes back and forth before it goes under, you have killed it and are free to pick the next tentacle to target.

The wrap mechanic has changed. You no longer hit the tentacle that is grabbing the boat. When she wraps, there should be one shorter tentacle, very close to the ship, that is "looking" at the tentacle that wrapped the ship. Hit it. After you hit this tentacle it will move to the other side of your boat. Do this 3-4 times to get it to unwrap. You can get 1-2 cannonballs on it before it switches sides. It takes a few seconds to switch so use this time to get an extra bail of water out of the ship or restock your cannonballs, etc.

Prioritize the holes in the bottom of the ship. You don't need to patch all of the wholes in the back of the sloop, especially if you are running low on planks. You can leave 1 to 2 and it won't leak too much. I don't like to leave more than 2 unfixed.

Don't worry about the loot floating in the water until she is dead. Getting off your ship as a solo is a death wish. If you are aggressive enough she will die relatively fast and you will be able to get all of the loot.

Lastly, some of it comes down to RNG. How many times does she slap the ship? How many hits does it take to get her to unwrap? How many times does she try to suck you off the ship? And, if you get attacked by something else while you are fighting Karen... good luck... haven't figured out the best strategy for that and I hope I don't have to.

@silentwish That's fair. I usually hide below deck and pop up briefly to check how close I am to the island when sailing for one to use this strategy. The only dangerous part is when raising the sails. You can always anchor and then raise and reposition if you need. Then once I'm parked it's not an issue to get knocked off.

This strategy can definitely impact the pace of the game but I have never had an experience where I am getting attacked that constantly that it becomes a problem. It really only takes 3-4 passes around the island for you to kill them. Also, if it is not a ship that emerged from underwater near you it will normally sail past your without shooting as long as you don't fire at them or get too close.