Unreliable Flaky Booting for Ubuntu 20.04

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I am trying to diagnose my problem booting Ubuntu 20.04 on my Dell Laptop. Recently, the booting on my system has become unreliable and flaky. Use of the GRUB recovery menu shows multiple kernels, probably due to updates. However, none of these work reliably, including the most recent.
Using the recovery mode seems to proceed okay without reporting any errors, and but resuming the boot seems to always fails.
The only thing that works now is updating GRUB from the recovery menu and then continuing the boot. What steps should I take to figure out what is going on?

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