Follow-up Comment #4, bug #40344 (project make):
Make does not necessarily prepend the current directory, but the library
functions it calls might do that internally, as part of file-name
normalization. (So it's not the current directory that counts, but
CURRENT_DIR/../../../../../../ in your case.) When they do that, and the
result exceeds 259 characters, all these functions fail due to the
limitation.
As for SUBST, you can use it to work around this because then the name will be
shorter, like X:/this-is-a-long-path-component-0/this-is-a-long-filename.txt.
Windows APIs never normalize file names beyond the drive letter, even if it is
a SUBSTed drive letter.
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