diff --git a/demos/main/src/main/res/values/strings.xml b/demos/main/src/main/res/values/strings.xml
index 9085c43bd3..49441ef7da 100644
--- a/demos/main/src/main/res/values/strings.xml
+++ b/demos/main/src/main/res/values/strings.xml
@@ -21,7 +21,7 @@
 
   <string name="unexpected_intent_action">Unexpected intent action: <xliff:g id="action">%1$s</xliff:g></string>
 
-  <string name="error_cleartext_not_permitted">Cleartext traffic not permitted</string>
+  <string name="error_cleartext_not_permitted">Cleartext HTTP traffic not permitted. See https://exoplayer.dev/issues/cleartext-not-permitted</string>
 
   <string name="error_generic">Playback failed</string>
 
diff --git a/extensions/cronet/src/main/java/com/google/android/exoplayer2/ext/cronet/CronetDataSource.java b/extensions/cronet/src/main/java/com/google/android/exoplayer2/ext/cronet/CronetDataSource.java
index 461d18fd26..b215b6d763 100644
--- a/extensions/cronet/src/main/java/com/google/android/exoplayer2/ext/cronet/CronetDataSource.java
+++ b/extensions/cronet/src/main/java/com/google/android/exoplayer2/ext/cronet/CronetDataSource.java
@@ -443,8 +443,14 @@ public class CronetDataSource extends BaseDataSource implements HttpDataSource {
     transferInitializing(dataSpec);
     try {
       boolean connectionOpened = blockUntilConnectTimeout();
-      if (exception != null) {
-        throw new OpenException(exception, dataSpec, getStatus(urlRequest));
+      @Nullable IOException connectionOpenException = exception;
+      if (connectionOpenException != null) {
+        @Nullable String message = connectionOpenException.getMessage();
+        if (message != null
+            && Util.toLowerInvariant(message).contains("err_cleartext_not_permitted")) {
+          throw new CleartextNotPermittedException(connectionOpenException, dataSpec);
+        }
+        throw new OpenException(connectionOpenException, dataSpec, getStatus(urlRequest));
       } else if (!connectionOpened) {
         // The timeout was reached before the connection was opened.
         throw new OpenException(new SocketTimeoutException(), dataSpec, getStatus(urlRequest));
diff --git a/extensions/okhttp/src/main/java/com/google/android/exoplayer2/ext/okhttp/OkHttpDataSource.java b/extensions/okhttp/src/main/java/com/google/android/exoplayer2/ext/okhttp/OkHttpDataSource.java
index 57fee20d04..85d3530e2d 100644
--- a/extensions/okhttp/src/main/java/com/google/android/exoplayer2/ext/okhttp/OkHttpDataSource.java
+++ b/extensions/okhttp/src/main/java/com/google/android/exoplayer2/ext/okhttp/OkHttpDataSource.java
@@ -242,6 +242,11 @@ public class OkHttpDataSource extends BaseDataSource implements HttpDataSource {
       responseBody = Assertions.checkNotNull(response.body());
       responseByteStream = responseBody.byteStream();
     } catch (IOException e) {
+      @Nullable String message = e.getMessage();
+      if (message != null
+          && Util.toLowerInvariant(message).matches("cleartext communication.*not permitted.*")) {
+        throw new CleartextNotPermittedException(e, dataSpec);
+      }
       throw new HttpDataSourceException(
           "Unable to connect", e, dataSpec, HttpDataSourceException.TYPE_OPEN);
     }
diff --git a/library/common/src/main/java/com/google/android/exoplayer2/upstream/HttpDataSource.java b/library/common/src/main/java/com/google/android/exoplayer2/upstream/HttpDataSource.java
index d2170b9eab..1c450ca02d 100644
--- a/library/common/src/main/java/com/google/android/exoplayer2/upstream/HttpDataSource.java
+++ b/library/common/src/main/java/com/google/android/exoplayer2/upstream/HttpDataSource.java
@@ -271,7 +271,24 @@ public interface HttpDataSource extends DataSource {
       this.dataSpec = dataSpec;
       this.type = type;
     }
+  }
 
+  /**
+   * Thrown when cleartext HTTP traffic is not permitted. For more information including how to
+   * enable cleartext traffic, see the <a
+   * href="https://exoplayer.dev/issues/cleartext-not-permitted">corresponding troubleshooting
+   * topic</a>.
+   */
+  final class CleartextNotPermittedException extends HttpDataSourceException {
+
+    public CleartextNotPermittedException(IOException cause, DataSpec dataSpec) {
+      super(
+          "Cleartext HTTP traffic not permitted. See"
+              + " https://exoplayer.dev/issues/cleartext-not-permitted",
+          cause,
+          dataSpec,
+          TYPE_OPEN);
+    }
   }
 
   /**
@@ -285,7 +302,6 @@ public interface HttpDataSource extends DataSource {
       super("Invalid content type: " + contentType, dataSpec, TYPE_OPEN);
       this.contentType = contentType;
     }
-
   }
 
   /**
diff --git a/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultHttpDataSource.java b/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultHttpDataSource.java
index d15804fd51..94c02c7e83 100644
--- a/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultHttpDataSource.java
+++ b/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultHttpDataSource.java
@@ -306,6 +306,11 @@ public class DefaultHttpDataSource extends BaseDataSource implements HttpDataSou
     try {
       connection = makeConnection(dataSpec);
     } catch (IOException e) {
+      @Nullable String message = e.getMessage();
+      if (message != null
+          && Util.toLowerInvariant(message).matches("cleartext http traffic.*not permitted.*")) {
+        throw new CleartextNotPermittedException(e, dataSpec);
+      }
       throw new HttpDataSourceException(
           "Unable to connect", e, dataSpec, HttpDataSourceException.TYPE_OPEN);
     }
diff --git a/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultLoadErrorHandlingPolicy.java b/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultLoadErrorHandlingPolicy.java
index dc5aefac6d..091c57de10 100644
--- a/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultLoadErrorHandlingPolicy.java
+++ b/library/core/src/main/java/com/google/android/exoplayer2/upstream/DefaultLoadErrorHandlingPolicy.java
@@ -19,6 +19,7 @@ import static java.lang.Math.min;
 
 import com.google.android.exoplayer2.C;
 import com.google.android.exoplayer2.ParserException;
+import com.google.android.exoplayer2.upstream.HttpDataSource.CleartextNotPermittedException;
 import com.google.android.exoplayer2.upstream.HttpDataSource.InvalidResponseCodeException;
 import com.google.android.exoplayer2.upstream.Loader.UnexpectedLoaderException;
 import java.io.FileNotFoundException;
@@ -86,14 +87,16 @@ public class DefaultLoadErrorHandlingPolicy implements LoadErrorHandlingPolicy {
 
   /**
    * Retries for any exception that is not a subclass of {@link ParserException}, {@link
-   * FileNotFoundException} or {@link UnexpectedLoaderException}. The retry delay is calculated as
-   * {@code Math.min((errorCount - 1) * 1000, 5000)}.
+   * FileNotFoundException}, {@link CleartextNotPermittedException} or {@link
+   * UnexpectedLoaderException}. The retry delay is calculated as {@code Math.min((errorCount - 1) *
+   * 1000, 5000)}.
    */
   @Override
   public long getRetryDelayMsFor(LoadErrorInfo loadErrorInfo) {
     IOException exception = loadErrorInfo.exception;
     return exception instanceof ParserException
             || exception instanceof FileNotFoundException
+            || exception instanceof CleartextNotPermittedException
             || exception instanceof UnexpectedLoaderException
         ? C.TIME_UNSET
         : min((loadErrorInfo.errorCount - 1) * 1000, 5000);