diff --git a/features/core.feature b/features/core.feature
index ab86da42..dd072ba4 100644
--- a/features/core.feature
+++ b/features/core.feature
@@ -58,3 +58,12 @@ Feature: Basic reading and writing to a journal
         When we run "jrnl -on 2013-06-10 -s"
         Then the output should be "2013-06-10 15:40 Life is good."
 
+    Scenario: Invalid color configuration
+        Given we use the config "invalid_color.yaml"
+        When we run "jrnl -on 2013-06-10 -s"
+        Then the output should be
+        """
+        [ERROR: date set to invalid color: not-a-color]
+        [ERROR: title set to invalid color: also-not-a-color]
+        2013-06-10 15:40 Life is good.
+        """
diff --git a/features/data/configs/invalid_color.yaml b/features/data/configs/invalid_color.yaml
new file mode 100644
index 00000000..4c2c78fc
--- /dev/null
+++ b/features/data/configs/invalid_color.yaml
@@ -0,0 +1,15 @@
+default_hour: 9
+default_minute: 0
+editor: ""
+encrypt: false
+highlight: true
+journals:
+  default: features/journals/simple.journal
+linewrap: 80
+tagsymbols: "@"
+template: false
+timeformat: "%Y-%m-%d %H:%M"
+indent_character: "|"
+colors:
+  date: not-a-color
+  title: also-not-a-color
diff --git a/features/data/configs/no_colors.yaml b/features/data/configs/no_colors.yaml
new file mode 100644
index 00000000..9111b561
--- /dev/null
+++ b/features/data/configs/no_colors.yaml
@@ -0,0 +1,12 @@
+default_hour: 9
+default_minute: 0
+editor: ""
+encrypt: false
+highlight: true
+journals:
+  default: features/journals/simple.journal
+linewrap: 80
+tagsymbols: "@"
+template: false
+timeformat: "%Y-%m-%d %H:%M"
+indent_character: "|"
diff --git a/features/steps/core.py b/features/steps/core.py
index ab9b90c6..fbe8fa08 100644
--- a/features/steps/core.py
+++ b/features/steps/core.py
@@ -8,6 +8,7 @@ from dateutil import parser as date_parser
 from ansiwrap import strip_color
 from collections import defaultdict
 import os
+import ast
 import json
 import yaml
 import keyring
@@ -234,12 +235,17 @@ def journal_doesnt_exist(context, journal_name="default"):
 @then('the config should have "{key}" set to "{value}"')
 @then('the config for journal "{journal}" should have "{key}" set to "{value}"')
 def config_var(context, key, value, journal=None):
-    t, value = value.split(":")
-    value = {
-        "bool": lambda v: v.lower() == "true",
-        "int": int,
-        "str": str
-    }[t](value)
+    if not value[0] == "{":
+        t, value = value.split(":")
+        value = {
+            "bool": lambda v: v.lower() == "true",
+            "int": int,
+            "str": str
+        }[t](value)
+    else:
+        # Handle value being a dictionary
+        value = ast.literal_eval(value)
+
     config = util.load_config(install.CONFIG_FILE_PATH)
     if journal:
         config = config["journals"][journal]
diff --git a/features/upgrade.feature b/features/upgrade.feature
index bce026b8..587102eb 100644
--- a/features/upgrade.feature
+++ b/features/upgrade.feature
@@ -13,7 +13,7 @@ Feature: Upgrading Journals from 1.x.x to 2.x.x
 
     Scenario: Upgrading a journal encrypted with jrnl 1.x
         Given we use the config "encrypted_old.json"
-        When we run "jrnl -n 1" and enter 
+        When we run "jrnl -n 1" and enter
             """
             Y
             bad doggie no biscuit
@@ -21,3 +21,8 @@ Feature: Upgrading Journals from 1.x.x to 2.x.x
             """
         Then we should see the message "Password"
         and the output should contain "2013-06-10 15:40 Life is good"
+
+    Scenario: Upgrading a config without colors to colors
+        Given we use the config "no_colors.yaml"
+        When we run "jrnl -n 1"
+        Then the config should have "colors" set to "{'date':'red', 'title':'blue'}"