"""
commit 1cc0ee7d9f6a2817918fafd24c18d8bb093a85d3
Author: Andrew Svetlov <andrew.svetlov@gmail.com>
Date:   Tue May 7 16:53:19 2019 -0400

    bpo-36801: Fix waiting in StreamWriter.drain for closing
    SSL transport (GH-13098)
"""

I reverted this change in 3.7:

commit c647ad9b51c59f71c02cd90c5e67d1b2768323ca (HEAD -> 3.7, upstream/3.7)
Author: Victor Stinner <victor.stinner@gmail.com>
Date:   Tue May 14 22:29:54 2019 +0200

    Revert "bpo-36801: Fix waiting in StreamWriter.drain for closing SSL transport (GH-13098)" (GH-13328)
    
    This reverts commit 93aa57ac6594d1cc30d147720fc8a7a4e1ca2d3e.

Without this revert, I was able to easily reproduce the failure. With the revert, I cannot reproduce it anymore:
https://github.com/python/cpython/pull/13328#issuecomment-492394753