diff --git a/lib/internal/repl.js b/lib/internal/repl.js
index 1a62414a49e95d..79ad79abe87f04 100644
--- a/lib/internal/repl.js
+++ b/lib/internal/repl.js
@@ -120,7 +120,15 @@ function setupHistory(repl, historyPath, oldHistoryPath, ready) {
 
     if (data) {
       repl.history = data.split(/[\n\r]+/, repl.historySize);
-    } else if (oldHistoryPath) {
+    } else if (oldHistoryPath === historyPath) {
+      // If pre-v3.0, the user had set NODE_REPL_HISTORY_FILE to
+      // ~/.node_repl_history, warn the user about it and proceed.
+      repl._writeToOutput(
+          '\nThe old repl history file has the same name and location as ' +
+          `the new one i.e., ${historyPath} and is empty.\nUsing it as is.\n`);
+      repl._refreshLine();
+
+    }  else if (oldHistoryPath) {
       // Grab data from the older pre-v3.0 JSON NODE_REPL_HISTORY_FILE format.
       repl._writeToOutput(
           '\nConverting old JSON repl history to line-separated history.\n' +
@@ -128,7 +136,13 @@ function setupHistory(repl, historyPath, oldHistoryPath, ready) {
       repl._refreshLine();
 
       try {
-        repl.history = JSON.parse(fs.readFileSync(oldHistoryPath, 'utf8'));
+        // Pre-v3.0, repl history was stored as JSON.
+        // Try and convert it to line separated history.
+        const oldReplJSONHistory = fs.readFileSync(oldHistoryPath, 'utf8');
+
+        // Only attempt to use the history if there was any.
+        if (oldReplJSONHistory) repl.history = JSON.parse(oldReplJSONHistory);
+
         if (!Array.isArray(repl.history)) {
           throw new Error('Expected array, got ' + typeof repl.history);
         }
diff --git a/test/fixtures/.empty-repl-history-file b/test/fixtures/.empty-repl-history-file
new file mode 100644
index 00000000000000..e69de29bb2d1d6
diff --git a/test/parallel/test-repl-persistent-history.js b/test/parallel/test-repl-persistent-history.js
index 10e0dedf53ec3e..9b4b3890aed6cb 100644
--- a/test/parallel/test-repl-persistent-history.js
+++ b/test/parallel/test-repl-persistent-history.js
@@ -66,6 +66,10 @@ const homedirErr = '\nError: Could not get the home directory.\n' +
                    'REPL session history will not be persisted.\n';
 const replFailedRead = '\nError: Could not open history file.\n' +
                        'REPL session history will not be persisted.\n';
+const sameHistoryFilePaths = '\nThe old repl history file has the same name ' +
+                             'and location as the new one i.e., ' +
+                             path.join(common.tmpDir, '.node_repl_history') +
+                             ' and is empty.\nUsing it as is.\n';
 // File paths
 const fixtures = path.join(common.testDir, 'fixtures');
 const historyFixturePath = path.join(fixtures, '.node_repl_history');
@@ -73,9 +77,9 @@ const historyPath = path.join(common.tmpDir, '.fixture_copy_repl_history');
 const historyPathFail = path.join(common.tmpDir, '.node_repl\u0000_history');
 const oldHistoryPath = path.join(fixtures, 'old-repl-history-file.json');
 const enoentHistoryPath = path.join(fixtures, 'enoent-repl-history-file.json');
+const emptyHistoryPath = path.join(fixtures, '.empty-repl-history-file');
 const defaultHistoryPath = path.join(common.tmpDir, '.node_repl_history');
 
-
 const tests = [{
   env: { NODE_REPL_HISTORY: '' },
   test: [UP],
@@ -93,6 +97,16 @@ const tests = [{
   test: [UP],
   expected: [prompt, replDisabled, prompt]
 },
+{
+  env: { NODE_REPL_HISTORY_FILE: emptyHistoryPath },
+  test: [UP],
+  expected: [prompt, convertMsg, prompt]
+},
+{
+  env: { NODE_REPL_HISTORY_FILE: defaultHistoryPath },
+  test: [UP],
+  expected: [prompt, sameHistoryFilePaths, prompt]
+},
 {
   env: { NODE_REPL_HISTORY: historyPath },
   test: [UP, CLEAR],