Separate rule in the "Medical" folder does not seem to process the file.
I confirmed, using "preview" that the rule matches. Its action moves the file away to its final destination, but that never happens.
The debug log shows lines like:
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2019-01-19 22:54:15.202 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:54:16.704 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:54:25.745 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:54:33.587 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:54:34.587 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:56:34.649 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/.DS_Store. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 22:56:42.732 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/.DS_Store. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 23:07:18.390 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
2019-01-19 23:07:18.390 HazelHelper[447] DEBUG: Ignoring event in directory /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf. Only need to check for changes 1 levels deep. Event is in directory 4 levels deep.
It seems that Hazel convinced itself that we do not need to look at this file until the year 4000:
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2019-01-19 23:07:18.391 HazelHelper[447] DEBUG: Error resolving symlinks for path /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf:, No such file or directory
path = "<ComNoodlesoft_NoodlePathSet: 0x7fe3b2f01010>\n /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/2003-10-31 Bill copy.pdf : 0\n /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf : 0\n";
2019-01-19 23:07:20.615 hazelworker[1583][PREDICTION] DEBUG: Predicted fire time for file: /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf and rule SHC Lab filer: 4000-12-31 16:00:00.000 Should poll: 0
2019-01-19 23:07:20.639 hazelworker[1583][PREDICTION] DEBUG: Predicted fire time for file: /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf and rule Dentist Filer: 4000-12-31 16:00:00.000 Should poll: 0
2019-01-19 23:07:20.641 hazelworker[1583][PREDICTION] DEBUG: Predicted fire time for file: /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf and rule Stryker filer: 4000-12-31 16:00:00.000 Should poll: 0
2019-01-19 23:07:20.680 hazelworker[1583][PREDICTION] DEBUG: Predicted fire time for file: /Users/dolf/Documents/Paperless/ To be Filed/Classified/Bills/Medical/Bill copy.pdf and rule Generic filer: 4000-12-31 16:00:00.000 Should poll: 0
2019-01-19 23:07:20.680 hazelworker[1583] DEBUG: Bill copy.pdf: Did not match any rules.
I have tried to "touch" the file to force processing. No good. I've also moved it out of the folder, copied it, and moved the copy back in (thinking it was a rest file). No good. I've tired modifying the file (as it was originally a copy on an AFS file system, so not a independent copy), thinking copy on write would kick in and make this a new file. No good.
The log commentary about 4 levels seems somewhat indicative of the likely culprit. The "Medical" folder is on level 4 if you count the original folder as level 1. However, I decided to move the "Medical" file to a location parallel to the " To Be Filed" folder. That gets rid of the level 1/4 stuff, but still no processing.
The only other thing I can say is that the rule that matches this file is rather large. It vertically fills up my screen on an iMac5K. It shouldn't matter, but perhaps it does.