diff --git a/features/shell.feature b/features/shell.feature
index d5595506..3fcf6ec8 100644
--- a/features/shell.feature
+++ b/features/shell.feature
@@ -77,3 +77,41 @@ Feature: WordPress REPL
       """
       history: -1: invalid option
       """
+
+  Scenario: Exception handling preserves session state
+    Given a WP install
+    And a session file:
+      """
+      $foo = 'test_value';
+      require 'nonexistent_file.txt';
+      echo $foo;
+      """
+
+    When I try `wp shell --basic < session`
+    Then STDOUT should contain:
+      """
+      test_value
+      """
+    And STDERR should contain:
+      """
+      Error: Failed opening required 'nonexistent_file.txt'
+      """
+
+  Scenario: Exception handling for expression errors
+    Given a WP install
+    And a session file:
+      """
+      $bar = 'preserved';
+      nonexistent_function();
+      $bar;
+      """
+
+    When I try `wp shell --basic < session`
+    Then STDOUT should contain:
+      """
+      string(9) "preserved"
+      """
+    And STDERR should contain:
+      """
+      Error: Call to undefined function nonexistent_function()
+      """
diff --git a/src/WP_CLI/Shell/REPL.php b/src/WP_CLI/Shell/REPL.php
index 99b8f1f8..5008adc4 100644
--- a/src/WP_CLI/Shell/REPL.php
+++ b/src/WP_CLI/Shell/REPL.php
@@ -29,8 +29,13 @@ public function start() {
 
 			if ( self::starts_with( self::non_expressions(), $line ) ) {
 				ob_start();
-				// phpcs:ignore Squiz.PHP.Eval.Discouraged -- This is meant to be a REPL, no way to avoid eval.
-				eval( $line );
+				try {
+					// phpcs:ignore Squiz.PHP.Eval.Discouraged -- This is meant to be a REPL, no way to avoid eval.
+					eval( $line );
+				} catch ( \Throwable $e ) {
+					// Display the error message but continue the session
+					fwrite( STDERR, get_class( $e ) . ': ' . $e->getMessage() . "\n" );
+				}
 				$out = (string) ob_get_clean();
 				if ( 0 < strlen( $out ) ) {
 					$out = rtrim( $out, "\n" ) . "\n";
@@ -43,8 +48,14 @@ public function start() {
 
 				// Write directly to STDOUT, to sidestep any output buffers created by plugins
 				ob_start();
-				// phpcs:ignore Squiz.PHP.Eval.Discouraged -- This is meant to be a REPL, no way to avoid eval.
-				$evl = eval( $line );
+				try {
+					// phpcs:ignore Squiz.PHP.Eval.Discouraged -- This is meant to be a REPL, no way to avoid eval.
+					$evl = eval( $line );
+				} catch ( \Throwable $e ) {
+					// Display the error message but continue the session
+					fwrite( STDERR, get_class( $e ) . ': ' . $e->getMessage() . "\n" );
+					$evl = null;
+				}
 				$out = (string) ob_get_clean();
 				if ( 0 < strlen( $out ) ) {
 					echo rtrim( $out, "\n" ) . "\n";