How do I know when to escalate a problem?

You are unsure when to escalate, so you swing between sitting on things too long and kicking up what you could have handled. That swing is uncomfortable, but it is normal for anyone who has not yet built the internal line for where their job ends. The line comes with experience, and it can be learned faster than you think. Most of the confusion clears with one simple test: escalate when the problem needs authority, access, or knowledge you do not have, and handle it when it only needs effort or time you do have. Write that test down. Check each case against it before you act. When you are genuinely unsure, set a small limit, say fifteen minutes or one honest attempt, then escalate if you are still stuck. That rule takes the agonizing out of the choice. Over time you will feel the line without checking. For now, let the rule carry it.