Here is how I solved 'Gotta Crack Them All' from the CSAW 2022 CTF.
After recording the video I decided to figure out how to decrypt the full flag. After the first round of decrypting I took the longest plain-text password that I could reliably guess the missing characters and then used the service to re-encrypt those. Using the same technique in the video, I was able to get more of the key and therefore correctly decrypt more of the passwords.