diff --git a/hadoop-tools/hadoop-azure/src/main/java/org/apache/hadoop/fs/azurebfs/services/AbfsRestOperation.java b/hadoop-tools/hadoop-azure/src/main/java/org/apache/hadoop/fs/azurebfs/services/AbfsRestOperation.java
index 24ec292664..584b71f1ee 100644
--- a/hadoop-tools/hadoop-azure/src/main/java/org/apache/hadoop/fs/azurebfs/services/AbfsRestOperation.java
+++ b/hadoop-tools/hadoop-azure/src/main/java/org/apache/hadoop/fs/azurebfs/services/AbfsRestOperation.java
@@ -34,7 +34,6 @@
 import org.apache.hadoop.fs.azurebfs.contracts.exceptions.AzureBlobFileSystemException;
 import org.apache.hadoop.fs.azurebfs.contracts.exceptions.InvalidAbfsRestOperationException;
 import org.apache.hadoop.fs.azurebfs.constants.HttpHeaderConfigurations;
-import org.apache.hadoop.fs.azurebfs.oauth2.AzureADAuthenticator.HttpException;
 
 /**
  * The AbfsRestOperation for Rest AbfsClient.
@@ -233,7 +232,13 @@ private boolean executeHttpOperation(final int retryCount) throws AzureBlobFileS
               hasRequestBody ? bufferLength : 0);
           break;
       }
+    } catch (IOException e) {
+      LOG.debug("Auth failure: {}, {}", method, url);
+      throw new AbfsRestOperationException(-1, null,
+          "Auth failure: " + e.getMessage(), e);
+    }
 
+    try {
       // dump the headers
       AbfsIoUtils.dumpHeadersToDebugLog("Request Headers",
           httpOperation.getConnection().getRequestProperties());
@@ -256,9 +261,7 @@ private boolean executeHttpOperation(final int retryCount) throws AzureBlobFileS
       }
     } catch (UnknownHostException ex) {
       String hostname = null;
-      if (httpOperation != null) {
-        hostname = httpOperation.getHost();
-      }
+      hostname = httpOperation.getHost();
       LOG.warn("Unknown host name: %s. Retrying to resolve the host name...",
           hostname);
       if (!client.getRetryPolicy().shouldRetry(retryCount, -1)) {
@@ -267,24 +270,13 @@ private boolean executeHttpOperation(final int retryCount) throws AzureBlobFileS
       return false;
     } catch (IOException ex) {
       if (LOG.isDebugEnabled()) {
-        if (httpOperation != null) {
-          LOG.debug("HttpRequestFailure: " + httpOperation.toString(), ex);
-        } else {
-          LOG.debug("HttpRequestFailure: " + method + "," + url, ex);
-        }
+        LOG.debug("HttpRequestFailure: {}, {}", httpOperation.toString(), ex);
       }
 
       if (!client.getRetryPolicy().shouldRetry(retryCount, -1)) {
         throw new InvalidAbfsRestOperationException(ex);
       }
 
-      // once HttpException is thrown by AzureADAuthenticator,
-      // it indicates the policy in AzureADAuthenticator determined
-      // retry is not needed
-      if (ex instanceof HttpException) {
-        throw new AbfsRestOperationException((HttpException) ex);
-      }
-
       return false;
     } finally {
       AbfsClientThrottlingIntercept.updateMetrics(operationType, httpOperation);
diff --git a/hadoop-tools/hadoop-azure/src/test/java/org/apache/hadoop/fs/azurebfs/ITestAbfsRestOperationException.java b/hadoop-tools/hadoop-azure/src/test/java/org/apache/hadoop/fs/azurebfs/ITestAbfsRestOperationException.java
index 1d86de7ebe..a71e7bc815 100644
--- a/hadoop-tools/hadoop-azure/src/test/java/org/apache/hadoop/fs/azurebfs/ITestAbfsRestOperationException.java
+++ b/hadoop-tools/hadoop-azure/src/test/java/org/apache/hadoop/fs/azurebfs/ITestAbfsRestOperationException.java
@@ -20,21 +20,31 @@
 
 import java.io.IOException;
 
+import org.assertj.core.api.Assertions;
+import org.junit.Assert;
+import org.junit.Test;
+
 import org.apache.hadoop.conf.Configuration;
+import org.apache.hadoop.fs.azurebfs.contracts.exceptions.AbfsRestOperationException;
+import org.apache.hadoop.fs.azurebfs.contracts.services.AzureServiceErrorCode;
 import org.apache.hadoop.fs.azurebfs.oauth2.RetryTestTokenProvider;
 import org.apache.hadoop.fs.FileStatus;
 import org.apache.hadoop.fs.FileSystem;
 import org.apache.hadoop.fs.Path;
 
-import org.junit.Assert;
-import org.junit.Test;
-
+import static org.apache.hadoop.fs.azurebfs.constants.AbfsHttpConstants.DOT;
+import static org.apache.hadoop.fs.azurebfs.constants.ConfigurationKeys.AZURE_CREATE_REMOTE_FILESYSTEM_DURING_INITIALIZATION;
+import static org.apache.hadoop.fs.azurebfs.constants.ConfigurationKeys.FS_AZURE_ACCOUNT_AUTH_TYPE_PROPERTY_NAME;
+import static org.apache.hadoop.fs.azurebfs.constants.ConfigurationKeys.FS_AZURE_ACCOUNT_TOKEN_PROVIDER_TYPE_PROPERTY_NAME;
+import static org.apache.hadoop.fs.azurebfs.constants.TestConfigurationKeys.FS_AZURE_ABFS_ACCOUNT_NAME;
 import static org.apache.hadoop.test.LambdaTestUtils.intercept;
 
 /**
  * Verify the AbfsRestOperationException error message format.
  * */
 public class ITestAbfsRestOperationException extends AbstractAbfsIntegrationTest{
+  private static final String RETRY_TEST_TOKEN_PROVIDER = "org.apache.hadoop.fs.azurebfs.oauth2.RetryTestTokenProvider";
+
   public ITestAbfsRestOperationException() throws Exception {
     super();
   }
@@ -114,4 +124,35 @@ public void testWithDifferentCustomTokenFetchRetry(int numOfRetries) throws Exce
             + ") done, does not match with fs.azure.custom.token.fetch.retry.count configured (" + numOfRetries
             + ")", RetryTestTokenProvider.reTryCount == numOfRetries);
   }
+
+  @Test
+  public void testAuthFailException() throws Exception {
+    Configuration config = new Configuration(getRawConfiguration());
+    String accountName = config
+        .get(FS_AZURE_ABFS_ACCOUNT_NAME);
+    // Setup to configure custom token provider
+    config.set(FS_AZURE_ACCOUNT_AUTH_TYPE_PROPERTY_NAME + DOT
+        + accountName, "Custom");
+    config.set(
+        FS_AZURE_ACCOUNT_TOKEN_PROVIDER_TYPE_PROPERTY_NAME + DOT + accountName,
+        RETRY_TEST_TOKEN_PROVIDER);
+    // Stop filesystem creation as it will lead to calls to store.
+    config.set(AZURE_CREATE_REMOTE_FILESYSTEM_DURING_INITIALIZATION, "false");
+
+    final AzureBlobFileSystem fs = getFileSystem(config);
+    try {
+      fs.getFileStatus(new Path("/"));
+      fail("Should fail at auth token fetch call");
+    } catch (AbfsRestOperationException e) {
+      String errorDesc = "Should throw RestOp exception on AAD failure";
+      Assertions.assertThat(e.getStatusCode())
+          .describedAs("Incorrect status code. " + errorDesc).isEqualTo(-1);
+      Assertions.assertThat(e.getErrorCode())
+          .describedAs("Incorrect error code. " + errorDesc)
+          .isEqualTo(AzureServiceErrorCode.UNKNOWN);
+      Assertions.assertThat(e.getErrorMessage())
+          .describedAs("Incorrect error message. " + errorDesc)
+          .contains("Auth failure: ");
+    }
+  }
 }
\ No newline at end of file