diff --git a/features/data/configs/upgrade_from_195_with_missing_journal.json b/features/data/configs/upgrade_from_195_with_missing_journal.json
new file mode 100644
index 00000000..8d456159
--- /dev/null
+++ b/features/data/configs/upgrade_from_195_with_missing_journal.json
@@ -0,0 +1,11 @@
+{
+"default_hour": 9,
+"timeformat": "%Y-%m-%d %H:%M",
+"linewrap": 80,
+"encrypt": false,
+"editor": "",
+"default_minute": 0,
+"highlight": true,
+"journals": {"default": "features/journals/simple_jrnl-1-9-5.journal", "missing":  "features/journals/missing.journal"},
+"tagsymbols": "@"
+}
diff --git a/features/upgrade.feature b/features/upgrade.feature
index b2c569c7..cbbb2d99 100644
--- a/features/upgrade.feature
+++ b/features/upgrade.feature
@@ -35,3 +35,16 @@ Feature: Upgrading Journals from 1.x.x to 2.x.x
             10.06.2013 15:40 He said "[this] is the best time to be alive".
             """
         Then the journal should have 2 entries
+
+    @skip_win
+    Scenario: Successful upgrade with missing journal
+        Given we use the config "upgrade_from_195_with_missing_journal.json"
+        When we run "jrnl -ls" and enter "Y Y"
+        Then we should see the message "Journal 'missing' created"
+        Then we should see the message "We're all done here"
+
+    @skip_win
+    Scenario: Aborted upgrade with missing journal
+        Given we use the config "upgrade_from_195_with_missing_journal.json"
+        When we run "jrnl -ls" and enter "Y N"
+        Then we should see the message "jrnl NOT upgraded, exiting."
\ No newline at end of file
diff --git a/jrnl/upgrade.py b/jrnl/upgrade.py
index e252d2d0..a630d3d4 100644
--- a/jrnl/upgrade.py
+++ b/jrnl/upgrade.py
@@ -11,10 +11,22 @@ import os
 def backup(filename, binary=False):
     print(f"  Created a backup at {filename}.backup", file=sys.stderr)
     filename = os.path.expanduser(os.path.expandvars(filename))
-    with open(filename, "rb" if binary else "r") as original:
-        contents = original.read()
-    with open(filename + ".backup", "wb" if binary else "w") as backup:
-        backup.write(contents)
+
+    try:
+        with open(filename, "rb" if binary else "r") as original:
+            contents = original.read()
+
+        with open(filename + ".backup", "wb" if binary else "w") as backup:
+            backup.write(contents)
+    except FileNotFoundError:
+        print(f"\nError: {filename} does not exist.")
+        try:
+            cont = util.yesno(f"\nCreate {filename}?", default=False)
+            if not cont:
+                raise KeyboardInterrupt
+
+        except KeyboardInterrupt:
+            raise UserAbort("jrnl NOT upgraded, exiting.")
 
 
 def upgrade_jrnl_if_necessary(config_path):
@@ -144,6 +156,7 @@ older versions of jrnl anymore.
         j.write()
 
     print("\nUpgrading config...", file=sys.stderr)
+
     backup(config_path)
 
     print("\nWe're all done here and you can start enjoying jrnl 2.", file=sys.stderr)