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At some point since the last time I used it (in the past few months), SQLAlchemy has stopped working on my MacBook Pro. I've boiled down the error to the following

from sqlalchemy import create_engine

Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/sqlalchemy/engine/", line 500, in create_engine
    return strategy.create(*args, **kwargs)
  File "/Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/sqlalchemy/engine/", line 87, in create
    dbapi = dialect_cls.dbapi(**dbapi_args)
  File "/Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/sqlalchemy/dialects/postgresql/", line 753, in dbapi
    import psycopg2
  File "/Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/psycopg2/", line 50, in <module>
    from psycopg2._psycopg import (                     # noqa
ImportError: dlopen(/Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/psycopg2/, 2): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
  Referenced from: /Users/pvandivier/.pyenv/versions/3.7.3/lib/python3.7/site-packages/psycopg2/
  Reason: image not found

Fair enough - I installed openssl 1.1 since the last time I used SQL Alchemy. Sadly however, removing openssl 1.1 as the default in my PATH (setting the default to LibreSSL 2.8.3) doesn't fix the issue. 

I also tried uninstalling and reinstalling SQL Alchemy (via `pip --no-cache-dir`) but this also did not fix the issue. 

[StackOverflow suggests]( that I should symlink back to openssl 1.0 (`brew switch openssl 1.0.2s`) - but a comment below this advice has proved sadly prophetic

> ...Homebrew will remove packages that are deprecated. Not sure when will this solution stop working – [tom10271]( [Dec 19 '19 at 2:33](

I do not have openssl 1.0 locally [^1] and it no longer appears to be available from Homebrew. Fortunately I can spelunk into homebrew-core and find the deprecated package.

@@@ answer 878

# the following snippet fetches the full homebrew commit history and 
#   gives us those commits that reference openssl 1.0
# I've saved the cached output as of 2020-10-01 (b291a9e32a) as a gist at the below link

pushd "$(brew --repo homebrew/core)"
git fetch --unshallow
git log --pretty=oneline --abbrev-commit | grep -i openssl | grep '1\.0' 

I'm nervous though - I was reticent to highjack the default OpenSSL install back when I did it because I didn't fully understand what all would be affected. And attempting to revert it here doesn't appear to fix this issue! Am I trying to [dig my way out of a hole]( with this approach?

As well a closer reading of [the SQL Alchemy docs]( reveals that I can highjack the [default `psycopg` driver]( Manually selecting `pg8000` as a driver does allow my code to run, but is [explicitly not recomended](

> The pg8000 dialect is **not tested as part of SQLAlchemy’s continuous integration** and may have unresolved issues. The recommended PostgreSQL dialect is psycopg2.

from sqlalchemy import create_engine

The `pg8000` engine creates successfully but has not been without issues as a drop-in replacement. Is there a "boxed" solution to installing openssl 1.0 for use only by SQL Alchemy (so I don't break _other_ other things)? Or is setting an alternate driver a better rabbit hole to follow?

[^1]: Which makes me wonder why this was _ever_ working months ago 🤔 Am I perhaps ["_barking up the wrong tree_"](

Top Answer
Frustratingly, I've been unable to re-install `psycopg2`, but I'm guessing that's a problem for another day (given the _beefy_ error message)

![Screenshot 2020-10-01 at 13.20.29.png](/image?hash=e6b8760f386bbaff94d9bbe98c5b51e0215d70db11007e8a33752543fc90960f)

However, upgrading `psycopg2-binary` from 2.8.4 to 2.8.6 appears to have ameliorated the issue for now.

![Screenshot 2020-10-01 at 13.22.08.png](/image?hash=1e05d2c3961acdc203e25e929d82084a7aacd18df647f0c89cd08a93bc04417f)

At least I don't need to perform tomfoolery with deprecated versions of openssl ¯\\\_(ツ)_/¯

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