Lost a big group (and with it the game) - how to play it safer?

After reading and posting in the topic Desperate moves when losing - etiquette question
I found the game which I was thinking of when I posted. I thought I had some solid territory on the right. Sure, some weaknesses, but I thought black could never have enough space to live in there so I didnt worry too much. Turned out, the weaknesses were much worse than I thought and black simply killed a huge part of my groups.
I’d be grateful of some helping comments how to secure my groups more without losing the initiative in the game.

I think B just found a very exploitable weakness in your groups. They had quite a few cutting points. I wouldn’t label these as desperate, but more just overlooked weaknesses.

In this example, I’m rated lower than you I know so this could be bad advice, but I think your atari at N14 (move 148) was a critical mistake. It let him finish the cut in an attempt to save one stone. Sometimes defending takes losing initiative, it’s weighing the risks. In this case, though, I think P13 would have been a stronger response to O13. If he captures that one stone, follow up with O14. He has to fill in at N13 or lose both stones, and you keep the initiative in exchange for only 4 points. This is still a valid reduction from B.

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There were no weaknesses at first. The trouble started when white played tenuki again and again to black’s approaches. Even to move 153, inside white’s territory, white plays 154 on the other side of the board.

Eventually, the balance tipped and black played a capture sequence - without playing away, of course.

To protect yourself against such tricks, make it a habit to respond to inside placements. Since you exchange one point of territory for one prisoner, you cannot lose anything.

You can even answer moves like black 141 just to be safe. If you do, black has only captured a half-point ko in sente (+1 point that white forfeits voluntarily to protect). Then you don’t have to worry about black’s new forcing move (atari).

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yup, lesson learned. Thanks @Animiral & @pbgarden