Long time DM. I have a group with a player who is very prone to "retcon actions" where they complain that their character would have "already had their weapon drawn" or would "know not to leave home without a torch". I attempted to incorporate these retcons into the game using "flashbacks" in the style of Blades In The Dark, but they were quickly abused to absurd effect. I implemented a currency that could be spent on flashbacks or rerolls or whatever, sort of like Inspiration or Hero Points but found that the complaining started up again as soon as the currency ran out.

I get that some players are keen to play out the *competence fantasy " where their heroes are always on top of things and for some games, I'm actually ok with it. But even for those games I feel at times that the amount of back pedaling and "I would have" takes some of the narrative tension away. This particular player is very reluctant to find themselves unprepared or taken completely off-guard by a situation. Worse, if I outline a "if you don't tell me about it before I describe what's next, then you'll have to work with what you did declare" rule, I will often hear complaints along the lines of "you didn't give me a chance to say it!"

How do you adjudicate this type of thing? Are you strict about what a player is holding and carrying or you do allow wiggle room? Have you dealt with a player who abuses that wiggle room? Thoughts?

Edit: to clarify, I was seeking general thoughts on how people handle this at their table and what they prefer as players under different circumstances. It may have seemed like I was asking Reddit to "fix my game" but I wasn't.