diff --git a/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/Gfsh.java b/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/Gfsh.java
index 14976a93531..a2f4fbf693f 100755
--- a/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/Gfsh.java
+++ b/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/Gfsh.java
@@ -23,6 +23,8 @@
 import java.io.IOException;
 import java.io.PrintStream;
 import java.net.URL;
+import java.nio.file.Files;
+import java.nio.file.Path;
 import java.nio.file.Paths;
 import java.text.MessageFormat;
 import java.util.ArrayList;
@@ -38,6 +40,7 @@
 import org.jline.reader.LineReader;
 import org.jline.reader.LineReaderBuilder;
 import org.jline.terminal.Terminal;
+import org.jline.terminal.TerminalBuilder;
 
 import org.apache.geode.annotations.internal.MakeNotStatic;
 import org.apache.geode.annotations.internal.MutableForTesting;
@@ -1094,6 +1097,9 @@ private void write(String message, boolean isError) {
   }
 
   protected LineReader createConsoleReader() {
+    // Check and migrate old history file format before creating LineReader
+    migrateHistoryFileIfNeeded();
+
     // Create GfshCompleter with our parser to enable TAB completion
     GfshCompleter completer = new GfshCompleter(this.parser);
 
@@ -1110,6 +1116,50 @@ protected LineReader createConsoleReader() {
     return lineReader;
   }
 
+  /**
+   * Checks if the history file exists and is in old JLine 2 format.
+   * If so, backs it up and creates a new empty history file.
+   */
+  private void migrateHistoryFileIfNeeded() {
+    try {
+      Path historyPath = Paths.get(getHistoryFileName());
+      if (!Files.exists(historyPath)) {
+        return;
+      }
+
+      // Check if file contains old format markers (lines starting with // or complex format)
+      java.util.List<String> lines = Files.readAllLines(historyPath);
+      boolean hasOldFormat = false;
+      for (String line : lines) {
+        String trimmed = line.trim();
+        // Old format had // comments and complex history format
+        if (trimmed.startsWith("//") || trimmed.startsWith("#")) {
+          hasOldFormat = true;
+          break;
+        }
+        // JLine 3 format should be simple: just command lines or :time:command format
+        // If we see anything complex, assume old format
+        if (trimmed.contains(":") && !trimmed.matches("^\\d+:\\d+:.*")) {
+          // Might be old format - be conservative and migrate
+          hasOldFormat = true;
+          break;
+        }
+      }
+
+      if (hasOldFormat) {
+        // Backup old history file
+        Path backupPath = historyPath.getParent()
+            .resolve(historyPath.getFileName().toString() + ".old");
+        Files.move(historyPath, backupPath,
+            java.nio.file.StandardCopyOption.REPLACE_EXISTING);
+        gfshFileLogger.info("Migrated old history file format. Backup saved to: " + backupPath);
+      }
+    } catch (IOException e) {
+      // Ignore - history migration is not critical
+      gfshFileLogger.warning("Could not migrate history file", e);
+    }
+  }
+
   protected void logCommandToOutput(String processedLine) {
     String originalString = expandedPropCommandsMap.get(processedLine);
     if (originalString != null) {
@@ -1589,10 +1639,27 @@ protected String expandProperties(final String input) {
   @Override
   public void run() {
     try {
+      // Initialize terminal and line reader before starting prompt loop
+      if (!isHeadlessMode) {
+        initializeTerminal();
+        createConsoleReader();
+      }
       printBannerAndWelcome();
       promptLoop();
     } catch (Exception e) {
       gfshFileLogger.severe("Error in shell main loop", e);
     }
   }
+
+  /**
+   * Initializes the JLine 3 Terminal for interactive shell use.
+   * This must be called before creating the LineReader.
+   */
+  private void initializeTerminal() throws IOException {
+    if (terminal == null) {
+      terminal = TerminalBuilder.builder()
+          .system(true)
+          .build();
+    }
+  }
 }
diff --git a/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/jline/GfshHistory.java b/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/jline/GfshHistory.java
index c967719c10a..77a5fc708e1 100644
--- a/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/jline/GfshHistory.java
+++ b/geode-gfsh/src/main/java/org/apache/geode/management/internal/cli/shell/jline/GfshHistory.java
@@ -28,6 +28,10 @@
  * Overrides JLine History to add History without newline characters.
  * Updated for JLine 3.x: extends DefaultHistory instead of MemoryHistory
  *
+ * <p>
+ * This implementation handles both old JLine 2 format history files (with timestamp comments)
+ * and new JLine 3 format. When loading an old format file, it will be converted to the new format.
+ *
  * @since GemFire 7.0
  */
 public class GfshHistory extends DefaultHistory {
@@ -60,6 +64,68 @@ public void setHistoryFilePath(Path path) {
     }
   }
 
+  /**
+   * Override attach to handle migration from old JLine 2 history format.
+   * If loading fails due to format issues, we'll backup the old file and start fresh.
+   */
+  @Override
+  public void attach(org.jline.reader.LineReader reader) {
+    try {
+      super.attach(reader);
+    } catch (Exception e) {
+      // Check if it's a history file format issue
+      Throwable cause = e;
+      while (cause != null) {
+        if (cause instanceof IllegalArgumentException
+            && cause.getMessage() != null
+            && cause.getMessage().contains("Bad history file syntax")) {
+          // Backup old history file and start fresh
+          migrateOldHistoryFile();
+          // Try again with clean file
+          try {
+            super.attach(reader);
+          } catch (Exception ex) {
+            // If still fails, just continue without history
+          }
+          return;
+        }
+        cause = cause.getCause();
+      }
+      // Re-throw if not a history format issue
+      if (e instanceof RuntimeException) {
+        throw (RuntimeException) e;
+      }
+      throw new RuntimeException(e);
+    }
+  }
+
+  /**
+   * Migrates old JLine 2 format history file to JLine 3 format.
+   * Backs up the old file and creates a new one with only the valid history entries.
+   */
+  private void migrateOldHistoryFile() {
+    if (historyFilePath == null || !Files.exists(historyFilePath)) {
+      return;
+    }
+
+    try {
+      // Backup old history file
+      Path backupPath = historyFilePath.getParent()
+          .resolve(historyFilePath.getFileName().toString() + ".old");
+      Files.move(historyFilePath, backupPath,
+          java.nio.file.StandardCopyOption.REPLACE_EXISTING);
+
+      // Create new history file with timestamp
+      try (BufferedWriter writer = Files.newBufferedWriter(historyFilePath,
+          StandardOpenOption.CREATE, StandardOpenOption.WRITE)) {
+        writer.write("# Migrated from old format on " + new java.util.Date());
+        writer.newLine();
+      }
+    } catch (IOException e) {
+      // Ignore - just start with empty history
+    }
+  }
+
   public void addToHistory(String buffer) {
     if (isAutoFlush()) {
       String redacted = ArgumentRedactor.redact(buffer.trim());