diff --git a/tests/features/password.feature b/tests/features/password.feature
index a5cbb0e1..23287b7c 100644
--- a/tests/features/password.feature
+++ b/tests/features/password.feature
@@ -77,3 +77,15 @@ Feature: Using the installed keyring
             2013-06-09 15:39 My first entry.
             2013-06-10 15:40 Life is good.
 
+
+    Scenario: Open encrypted journal when keyring exists but fails
+    # This should ask the user for the password after the keyring fails
+        Given we use the config "encrypted.yaml"
+        And we have a failed keyring
+        And we use the password "bad doggie no biscuit" if prompted
+        When we run "jrnl -n 1"
+        Then we should get no error
+        And we should be prompted for a password
+        And the output should contain "Failed to retrieve keyring"
+        And the output should contain "2013-06-10 15:40 Life is good"
+
diff --git a/tests/step_defs/conftest.py b/tests/step_defs/conftest.py
index c1046ef3..e15f265f 100644
--- a/tests/step_defs/conftest.py
+++ b/tests/step_defs/conftest.py
@@ -149,8 +149,8 @@ def journal_name():
 
 
 @fixture
-def output_to_error():
-    return False
+def which_output_stream():
+    return None
 
 
 # ----- STEPS ----- #
@@ -256,13 +256,21 @@ def output_should_match(regex, cli_run):
 @then(parse("the output should contain\n{output}"))
 @then(parse('the output should contain "{output}"'))
 @then('the output should contain "<output>"')
-@then(parse("the {output_to_error} output should contain\n{output}"))
-@then(parse('the {output_to_error} output should contain "{output}"'))
-def output_should_contain(output, output_to_error, cli_run):
-    assert output and (
-        (output_to_error and output in cli_run["stderr"])
-        or (not output_to_error and output in cli_run["stdout"])
-    )
+@then(parse("the {which_output_stream} output should contain\n{output}"))
+@then(parse('the {which_output_stream} output should contain "{output}"'))
+def output_should_contain(output, which_output_stream, cli_run):
+    assert output
+    if which_output_stream is None:
+        assert (output in cli_run["stdout"]) or (output in cli_run["stderr"])
+
+    elif which_output_stream == "standard":
+        assert output in cli_run["stdout"]
+
+    elif which_output_stream == "error":
+        assert output in cli_run["stderr"]
+
+    else:
+        assert output in cli_run[which_output_stream]
 
 
 @then(parse("the output should not contain\n{output}"))