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    //ad.company.com/shared vs //ad.company.com/Shared - I know windows in most part is case insensitive, but, it's still a difference in what you are doing Commented Sep 24 at 21:51
  • @Bravo, I've tested various casing combinations with both smbclient and with mount -t cifs, and they don't appear to affect the observed behavior. For example, smbclient still works if I spell it as sHaReD, and mount -t cifs still fails in the same way. Commented Sep 24 at 23:09
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    @ChrisDavies, yes, I tried that too (as described above, "Removing the prefixpath=Sites/BLAH") and I get the same error(s) from mount.cifs: random variation between Required key not available or No such file or directory. Added a few more details to clarify that I tried these already. Commented Sep 25 at 16:36
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    are there any additional messages in dmesg? (might require CONFIG_CIFS_DEBUG to be set in kernel configuration) Commented Sep 29 at 19:22
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    are you by chance using 6.6 kernel? github.com/NixOS/nixpkgs/issues/265521 (or more generic, perhaps an issue with your dns resolver?) Commented Sep 29 at 20:05