diff --git a/packages/flutter_tools/lib/src/android/gradle.dart b/packages/flutter_tools/lib/src/android/gradle.dart
index 853d81e463..940c655cf5 100644
--- a/packages/flutter_tools/lib/src/android/gradle.dart
+++ b/packages/flutter_tools/lib/src/android/gradle.dart
@@ -205,6 +205,7 @@ class AndroidGradleBuilder implements AndroidBuilder {
       isBuildingBundle: false,
       localGradleErrors: gradleErrors,
       configOnly: configOnly,
+      maxRetries: 1,
     );
   }
 
@@ -227,6 +228,7 @@ class AndroidGradleBuilder implements AndroidBuilder {
       validateDeferredComponents: validateDeferredComponents,
       deferredComponentsEnabled: deferredComponentsEnabled,
       configOnly: configOnly,
+      maxRetries: 1,
     );
   }
 
diff --git a/packages/flutter_tools/lib/src/android/gradle_errors.dart b/packages/flutter_tools/lib/src/android/gradle_errors.dart
index cfbb6c88c5..4d48be20f3 100644
--- a/packages/flutter_tools/lib/src/android/gradle_errors.dart
+++ b/packages/flutter_tools/lib/src/android/gradle_errors.dart
@@ -84,6 +84,7 @@ final List<GradleHandledError> gradleErrors = <GradleHandledError>[
   sslExceptionHandler,
   zipExceptionHandler,
   incompatibleJavaAndGradleVersionsHandler,
+  remoteTerminatedHandshakeHandler,
 ];
 
 const String _boxTitle = 'Flutter Fix';
@@ -700,3 +701,22 @@ final GradleHandledError incompatibleJavaAndGradleVersionsHandler = GradleHandle
   },
   eventLabel: 'incompatible-java-gradle-version',
 );
+
+@visibleForTesting
+final GradleHandledError remoteTerminatedHandshakeHandler = GradleHandledError(
+  test: (String line) => line.contains('Remote host terminated the handshake'),
+  handler: ({
+    required String line,
+    required FlutterProject project,
+    required bool usesAndroidX,
+    required bool multidexEnabled,
+  }) async {
+    globals.printError(
+      '${globals.logger.terminal.warningMark} '
+      'Gradle threw an error while downloading artifacts from the network.'
+    );
+
+    return GradleBuildStatus.retry;
+  },
+  eventLabel: 'remote-terminated-handshake',
+);
diff --git a/packages/flutter_tools/test/general.shard/android/gradle_errors_test.dart b/packages/flutter_tools/test/general.shard/android/gradle_errors_test.dart
index 419de4d8f3..015897e18f 100644
--- a/packages/flutter_tools/test/general.shard/android/gradle_errors_test.dart
+++ b/packages/flutter_tools/test/general.shard/android/gradle_errors_test.dart
@@ -49,6 +49,7 @@ void main() {
           sslExceptionHandler,
           zipExceptionHandler,
           incompatibleJavaAndGradleVersionsHandler,
+          remoteTerminatedHandshakeHandler,
         ])
       );
     });
@@ -88,6 +89,50 @@ at org.gradle.wrapper.GradleWrapperMain.main(GradleWrapperMain.java:61)''';
       ProcessManager: () => processManager,
     });
 
+    testUsingContext('retries if remote host terminated ssl handshake', () async {
+      const String errorMessage = r'''
+Exception in thread "main" javax.net.ssl.SSLHandshakeException: Remote host terminated the handshake
+	at java.base/sun.security.ssl.SSLSocketImpl.handleEOF(SSLSocketImpl.java:1696)
+	at java.base/sun.security.ssl.SSLSocketImpl.decode(SSLSocketImpl.java:1514)
+	at java.base/sun.security.ssl.SSLSocketImpl.readHandshakeRecord(SSLSocketImpl.java:1416)
+	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:456)
+	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:427)
+	at java.base/sun.net.www.protocol.https.HttpsClient.afterConnect(HttpsClient.java:572)
+	at java.base/sun.net.www.protocol.https.AbstractDelegateHttpsURLConnection.connect(AbstractDelegateHttpsURLConnection.java:197)
+	at java.base/sun.net.www.protocol.http.HttpURLConnection.followRedirect0(HttpURLConnection.java:2783)
+	at java.base/sun.net.www.protocol.http.HttpURLConnection.followRedirect(HttpURLConnection.java:2695)
+	at java.base/sun.net.www.protocol.http.HttpURLConnection.getInputStream0(HttpURLConnection.java:1854)
+	at java.base/sun.net.www.protocol.http.HttpURLConnection.getInputStream(HttpURLConnection.java:1520)
+	at java.base/sun.net.www.protocol.https.HttpsURLConnectionImpl.getInputStream(HttpsURLConnectionImpl.java:250)
+	at org.gradle.wrapper.Download.downloadInternal(Download.java:58)
+	at org.gradle.wrapper.Download.download(Download.java:44)
+	at org.gradle.wrapper.Install$1.call(Install.java:61)
+	at org.gradle.wrapper.Install$1.call(Install.java:48)
+	at org.gradle.wrapper.ExclusiveFileAccessManager.access(ExclusiveFileAccessManager.java:65)
+	at org.gradle.wrapper.Install.createDist(Install.java:48)
+	at org.gradle.wrapper.WrapperExecutor.execute(WrapperExecutor.java:128)
+	at org.gradle.wrapper.GradleWrapperMain.main(GradleWrapperMain.java:61)
+Caused by: java.io.EOFException: SSL peer shut down incorrectly
+	at java.base/sun.security.ssl.SSLSocketInputRecord.read(SSLSocketInputRecord.java:483)
+	at java.base/sun.security.ssl.SSLSocketInputRecord.readHeader(SSLSocketInputRecord.java:472)
+	at java.base/sun.security.ssl.SSLSocketInputRecord.decode(SSLSocketInputRecord.java:160)
+	at java.base/sun.security.ssl.SSLTransport.decode(SSLTransport.java:111)
+	at java.base/sun.security.ssl.SSLSocketImpl.decode(SSLSocketImpl.java:1506)''';
+
+      expect(formatTestErrorMessage(errorMessage, remoteTerminatedHandshakeHandler), isTrue);
+      expect(await remoteTerminatedHandshakeHandler.handler(
+        line: '',
+        multidexEnabled: true,
+        project: FakeFlutterProject(),
+        usesAndroidX: true,
+      ), equals(GradleBuildStatus.retry));
+
+      expect(testLogger.errorText,
+        contains(
+          'Gradle threw an error while downloading artifacts from the network.'
+        )
+      );
+    });
     testUsingContext('retries if gradle fails downloading with proxy error', () async {
       const String errorMessage = r'''
 Exception in thread "main" java.io.IOException: Unable to tunnel through proxy. Proxy returns "HTTP/1.1 400 Bad Request"