I'm having trouble reading tone, causing annoyance.

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In particular, with a close friend of mine. They often say things in a joke manner, that if taken literally would be offensive, unfortunately even though I am aware of this I find it hard to tell when they are joking. To complicate it further, they also seem to end sentences as questions even when they are not questions, so I end up getting irritated with them because I'm irritated at myself for finding understanding them so difficult.

Quite a common error for me was when they said things like "I see what you are doing" (when I was avoiding smokers because of asthma they said this to me) and it kept coming across to me as "Why are you doing that? You are doing something bad" because of the way it was said. It seemed to me like a punishing tone, rather than a simple statement being made. However, I realise it wasn't intended that way.

My other friend thinks this might have been because we were around a lot of people and social interaction is often harder to read with more people around, but I don't think it was because of that since I often struggle to tell when my friend is being sincere or not, and my other friend agreed that he can be hard to understand at times so I'm not sure if it's a communication error on his part or mine. I guess both.

Usually this doesn't cause issues because they are well aware that I often struggle to pick up on when they are being insincere, but it was today because I felt particularly annoyed with myself and ending up taking it out on them a bit. Sometimes I take it too far, we insult each other in a jokey way but I can overstep my bounds at times.

Anyone relate at all?

If you normally get along fine with this person, then it's a "reading tone" thing.
If this person has a tendency to make you feel bad most of the time,
then trust your gut, it's likely that he or she is the one causing the trouble.

Thing is, as an outsider, it's hard for me to judge.

It sounds like you usually get along well with your friend?