I may have posted a note months ago about this.

When forking off a constant level of 15-50 concurrent http requests
through polipo, polipo will lock up and/or fail to properly close
down the connection, filehandles, sockets, etc. If I recall, there
were lots of TIME_WAIT2's, I think, don't quote me. Whatever state
it was, it showed up in fstat, sockstat and netstat -a on FreeBSD 8.x
i386. My parent at the time was Tor. I wasn't able to track it down, it
occurred seemingly at random, with maybe 15% of the production runs
working fine.  When it locked, no further connections would go
through polipo thus requiring a kill. Also, polipo would often fail
to proxy reliably as indicated by wget's logged retry count of 2
or more, often into the 5-15 range. The OS and stack itself was
working just fine throughout. All software was current.  Polipo was
simply not suitable for production as far as I could make of it.
Then I pointed the same parallel fetching script at Privoxy via the
same http_proxy environment variables and the problem disappeared.
Been using Privoxy ever since but thought I should give people here
a heads up as to this experience.

You might be able to replicate by fetching the Alexa top 100 in round
robin via Tor in parallel concurrency settings from 15-50 or so till it jams
up.

proxyAddress=127.0.0.1
proxyPort=8080
socksParentProxy=127.0.0.1:9050
socksProxyType=socks5
allowedPorts=0-65535
localDocumentRoot=
disableConfiguration=true
disableServersList=false
forbiddenTunnelsFile=
forbiddenFile=
diskCacheRoot=
uncachableFile=
logLevel=0xFF

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