diff --git a/features/encryption.feature b/features/encryption.feature
index ebb3cc02..82d971eb 100644
--- a/features/encryption.feature
+++ b/features/encryption.feature
@@ -29,14 +29,3 @@
             When we run "jrnl simple -n 1"
             Then we should not see the message "Password"
             and the output should contain "2013-06-10 15:40 Life is good"
-
-        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 
-                """
-                Y
-                bad doggie no biscuit
-                bad doggie no biscuit
-                """
-            Then we should see the message "Password"
-            and the output should contain "2013-06-10 15:40 Life is good"
diff --git a/features/regression.feature b/features/regression.feature
index 21078a1c..3e644b19 100644
--- a/features/regression.feature
+++ b/features/regression.feature
@@ -43,17 +43,6 @@ Feature: Zapped bugs should stay dead.
             | Hope to get a lot of traffic.
             """
 
-    Scenario: Upgrade and parse journals with square brackets
-        Given we use the config "upgrade_from_195.json"
-        When we run "jrnl -9" and enter "Y"
-        Then the output should contain
-            """
-            2010-06-10 15:00 A life without chocolate is like a bad analogy.
-
-            2013-06-10 15:40 He said "[this] is the best time to be alive".
-            """
-        Then the journal should have 2 entries
-
     Scenario: Integers in square brackets should not be read as dates 
         Given we use the config "brackets.yaml"
         When we run "jrnl -1"
diff --git a/features/upgrade.feature b/features/upgrade.feature
new file mode 100644
index 00000000..bce026b8
--- /dev/null
+++ b/features/upgrade.feature
@@ -0,0 +1,23 @@
+Feature: Upgrading Journals from 1.x.x to 2.x.x
+
+    Scenario: Upgrade and parse journals with square brackets
+        Given we use the config "upgrade_from_195.json"
+        When we run "jrnl -9" and enter "Y"
+        Then the output should contain
+            """
+            2010-06-10 15:00 A life without chocolate is like a bad analogy.
+
+            2013-06-10 15:40 He said "[this] is the best time to be alive".
+            """
+        Then the journal should have 2 entries
+
+    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 
+            """
+            Y
+            bad doggie no biscuit
+            bad doggie no biscuit
+            """
+        Then we should see the message "Password"
+        and the output should contain "2013-06-10 15:40 Life is good"
diff --git a/jrnl/Journal.py b/jrnl/Journal.py
index cf336bdc..7feb49a6 100644
--- a/jrnl/Journal.py
+++ b/jrnl/Journal.py
@@ -84,9 +84,20 @@ class Journal(object):
     def write(self, filename=None):
         """Dumps the journal into the config file, overwriting it"""
         filename = filename or self.config['journal']
-        text = "\n".join([e.__unicode__() for e in self.entries])
+        text = self._to_text()
         self._store(filename, text)
 
+    def validate_parsing(self):
+        """Confirms that the jrnl is still parsed correctly after being dumped to text."""
+        new_entries = self._parse(self._to_text())
+        for i, entry in enumerate(self.entries):
+            if entry != new_entries[i]:
+                return False
+        return True
+
+    def _to_text(self):
+        return "\n".join([e.__unicode__() for e in self.entries])
+
     def _load(self, filename):
         raise NotImplementedError
 
diff --git a/jrnl/upgrade.py b/jrnl/upgrade.py
index 3784c9f6..1f4f999a 100644
--- a/jrnl/upgrade.py
+++ b/jrnl/upgrade.py
@@ -44,6 +44,7 @@ older versions of jrnl anymore.
     encrypted_journals = {}
     plain_journals = {}
     other_journals = {}
+    all_journals = []
 
     for journal_name, journal_conf in config['journals'].items():
         if isinstance(journal_conf, dict):
@@ -85,17 +86,27 @@ older versions of jrnl anymore.
         util.prompt("\nUpgrading encrypted '{}' journal stored in {}...".format(journal_name, path))
         backup(path, binary=True)
         old_journal = Journal.open_journal(journal_name, util.scope_config(config, journal_name), legacy=True)
-        new_journal = EncryptedJournal.from_journal(old_journal)
-        new_journal.write()
-        util.prompt("  Done.")
+        all_journals.append(EncryptedJournal.from_journal(old_journal))
 
     for journal_name, path in plain_journals.items():
         util.prompt("\nUpgrading plain text '{}' journal stored in {}...".format(journal_name, path))
         backup(path)
         old_journal = Journal.open_journal(journal_name, util.scope_config(config, journal_name), legacy=True)
-        new_journal = Journal.PlainJournal.from_journal(old_journal)
-        new_journal.write()
-        util.prompt("  Done.")
+        all_journals.append(Journal.PlainJournal.from_journal(old_journal))
+
+    # loop through lists to validate
+    failed_journals = [j for j in all_journals if not j.validate_parsing()]
+    if len(failed_journals) > 0:
+        util.prompt("\nThe following journal{} failed to upgrade:\n{}".format(
+            's' if len(failed_journals) > 1 else '', "\n".join(j.name for j in failed_journals))
+        )
+
+        util.prompt("Aborting upgrade.")
+        return
+
+    # write all journals - or - don't
+    for j in all_journals:
+        j.write()
 
     util.prompt("\nUpgrading config...")
     backup(config_path)