It's hard to overstate the value of an early question.
Asking the right clarifying question, early on in the task, can be the difference between wasting hours on something or finding a simple solution.
But sometimes, it can be difficult to know if you're asking a good question or if the team will find your question annoying. Luckily, I've found a quick strategy that helps me...
Write out the question, but don't send it. Then, look at every assumption in the question - are you sure about the answers? Is there a way you could verify your understanding?
Once you're reasonably sure you understand the pieces of your question, you can feel confident asking it. The answer isn't obviously in front of you, so nobody will blame you for asking.
Think of good questions early in the process. Write them down & try to answer them yourself before sending the message. But don't be afraid to send the message soon if the answer isn't obvious.