Can no longer program? Could before!

Development Tools Uploading
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I am having trouble programming my ESP32 Wroom 32d board. It worked well enough about a month ago but now it just times out.

It used to be I would click upload, then hold the boot button and release when it started uploading.

Now It just times out. To make things stranger, I can still COMMUNICATE with the ESP32. If it's not in download mode I can use the serial monitor and see the sketch running.

Really at a loss here.

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What sketch?
What is the running sketch showing?
How did the running sketch get uploaded if uploading times out?
What indications are you seeing that indicate timeout?
Does the IDE report any errors?

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