In MongoDB 4.0, multi document transactions does not work with GridFS because:
- Transaction is represented in single oplog entry, must be within 16MB limit.
- Default transaction lifetime is only 60 seconds (big files could take a while to upload). Increasing this default is going to affect WT cache pressure.
GridFS with transaction would be a very special case (I don't know if there's any yet). 
In PyMongo case, if a `ClientSession` is provided it will attempt to create an index for `fs.files` and `fs.chunks` collections grid_file.pyL196, currently creating an index in a transaction is prohibited in the server. 
- depends on
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                    DRIVERS-2062 Modify GridFS spec to support sessions, transactions and causal consistency -         
- Backlog
 
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- is related to
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                    JAVA-4887 GridFS doesn't support multi-document transactions -         
- Closed
 
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                    PYTHON-1332 Implement Drivers Sessions API -         
- Closed
 
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                    PYTHON-2244 Update documentation to promote GridFSBucket over GridFS -         
- Backlog
 
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                    PYTHON-2243 Raise informative error message when attempting a GridFS operation in a transaction -         
- Closed
 
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- related to
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                    JAVA-4890 Multidocument transaction support in GridFS -         
- Blocked
 
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