Author jeff.allen
Recipients Vikhe, jeff.allen
Date 2019-12-24.17:30:10
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It works for me at the prompt (Windows 10, Jython 2.7.2b2, pip 19.1), on a clean installation:

PS issue2852> inst\bin\pip install requests
PS issue2852> inst\bin\jython
Jython 2.7.2b2 (v2.7.2b2:b9b60766cabe, Nov 1 2019, 07:46:45)
[Java HotSpot(TM) 64-Bit Server VM (Oracle Corporation)] on java1.8.0_231
Type "help", "copyright", "credits" or "license" for more information.
>>> import requests
>>> import sys
>>> sys.path
['', '...\\issue2852\\inst\\Lib', '__classpath__', '__pyclasspath__/', '...\\.local\\lib\\jython2.7\\site-packages', '...\\issue2852\\inst\\Lib\\site-packages']

And the same from Java. On a quick check, also good on Jython 2.7.1. Argument -v to Jython will give you more information about where it looks during import (and -vv even more).

You don't need to work so hard on the sys.path: you can see Jython has already done it.
Date User Action Args
2019-12-24 17:30:11jeff.allensetmessageid: <>
2019-12-24 17:30:11jeff.allensetrecipients: + jeff.allen, Vikhe
2019-12-24 17:30:11jeff.allenlinkissue2852 messages
2019-12-24 17:30:10jeff.allencreate