I have some code with a testcase for it. It works fine.

import pysftp
from unittest import mock

remote_file_name = 'remote_file_name'
local_path = 'local/path/to/file'

def open_sftp_connection(hostname):
    return pysftp.Connection(hostname, username='usr', password='pswd')

def sftp_upload_try(local_path, dest_file_name):
    sftp_conn = None
    try:
        sftp_conn = open_sftp_connection('sftp-host')
        sftp_conn.put(local_path, remotepath=dest_file_name)
    finally:
        if sftp_conn:
            sftp_conn.close()

def test_sftp_try():
    conn_mock = mock.MagicMock()
    with mock.patch('test_sftp.open_sftp_connection', return_value=conn_mock):
        sftp_upload_try(local_path, remote_file_name)
        print(conn_mock.mock_calls)
        assert 1 == conn_mock.put.call_count
        assert remote_file_name == conn_mock.put.call_args.kwargs['remotepath']
        assert 1 == conn_mock.close.call_count

print(conn_mock.mock_calls) prints:

[call.put('local/path/to/file', remotepath='remote_file_name'),
 call.__bool__(),
 call.close()]

Instead of try-finally, I would like to use with:

def sftp_upload_with(local_path, dest_file_name):
    with open_sftp_connection('sftp-host') as sftp_conn:
        sftp_conn.put(f'${local_path}', remotepath=dest_file_name)

def test_sftp_with():
    conn_mock = mock.MagicMock()
    with mock.patch('test_sftp.open_sftp_connection', return_value=conn_mock):
        sftp_upload_with(local_path, remote_file_name)
        print(conn_mock.mock_calls)
        put_call = next(c for c in conn_mock.mock_calls if '__enter__().put' == c[0])
        assert put_call
        assert remote_file_name == put_call.kwargs['remotepath']

This time print(conn_mock.mock_calls) prints:

[call.__enter__(),
 call.__enter__().put('$local/path/to/file', remotepath='remote_file_name'),
 call.__exit__(None, None, None)]

So question is, is there some elegant way to assert calls when using with? Or do I have to do something ugly like '__enter__().put' == c[0] ?