Dahlia: I can confirm that if you create a simple directory that the parent of that directory isn't being marked stale in the cache. Isteana pointed out a very similar problem with plain files and I fixed that in 7.7.3, but looks like the same thing is happening with dirs as well...
I should point out that if you are using a zipscript the problem is mitigated because the creation of the incomplete symlinks in the parent dir after the first file is uploaded usually forces the cache to be updated...
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