diff --git a/sdk/storage/Azure.Storage.Blobs/src/BlockBlobClient.cs b/sdk/storage/Azure.Storage.Blobs/src/BlockBlobClient.cs
index 38c3186c13f4c..0a90c66c851b8 100644
--- a/sdk/storage/Azure.Storage.Blobs/src/BlockBlobClient.cs
+++ b/sdk/storage/Azure.Storage.Blobs/src/BlockBlobClient.cs
@@ -875,14 +875,36 @@ internal virtual async Task<Response<BlobContentInfo>> UploadInternal(
                     scope.Start();
                     Errors.VerifyStreamPosition(content, nameof(content));
 
-                    // compute hash BEFORE attaching progress handler
-                    ContentHasher.GetHashResult hashResult = await ContentHasher.GetHashOrDefaultInternal(
-                        content,
-                        validationOptions,
-                        async,
-                        cancellationToken).ConfigureAwait(false);
-
-                    content = content?.WithNoDispose().WithProgress(progressHandler);
+                    ContentHasher.GetHashResult hashResult = null;
+                    long contentLength = (content?.Length - content?.Position) ?? 0;
+                    long? structuredContentLength = default;
+                    string structuredBodyType = null;
+                    if (content != null &&
+                        validationOptions != null &&
+                        validationOptions.ChecksumAlgorithm.ResolveAuto() == StorageChecksumAlgorithm.StorageCrc64 &&
+                        validationOptions.PrecalculatedChecksum.IsEmpty &&
+                        ClientSideEncryption == null) // don't allow feature combination
+                    {
+                        // report progress in terms of caller bytes, not encoded bytes
+                        structuredContentLength = contentLength;
+                        structuredBodyType = Constants.StructuredMessage.CrcStructuredMessage;
+                        content = content.WithNoDispose().WithProgress(progressHandler);
+                        content = new StructuredMessageEncodingStream(
+                            content,
+                            Constants.StructuredMessage.DefaultSegmentContentLength,
+                            StructuredMessage.Flags.StorageCrc64);
+                        contentLength = content.Length - content.Position;
+                    }
+                    else
+                    {
+                        // compute hash BEFORE attaching progress handler
+                        hashResult = await ContentHasher.GetHashOrDefaultInternal(
+                            content,
+                            validationOptions,
+                            async,
+                            cancellationToken).ConfigureAwait(false);
+                        content = content.WithNoDispose().WithProgress(progressHandler);
+                    }
 
                     ResponseWithHeaders<BlockBlobUploadHeaders> response;
 
@@ -921,6 +943,8 @@ internal virtual async Task<Response<BlobContentInfo>> UploadInternal(
                             legalHold: legalHold,
                             transactionalContentMD5: hashResult?.MD5AsArray,
                             transactionalContentCrc64: hashResult?.StorageCrc64AsArray,
+                            structuredBodyType: structuredBodyType,
+                            structuredContentLength: structuredContentLength,
                             cancellationToken: cancellationToken)
                             .ConfigureAwait(false);
                     }
@@ -953,6 +977,8 @@ internal virtual async Task<Response<BlobContentInfo>> UploadInternal(
                             legalHold: legalHold,
                             transactionalContentMD5: hashResult?.MD5AsArray,
                             transactionalContentCrc64: hashResult?.StorageCrc64AsArray,
+                            structuredBodyType: structuredBodyType,
+                            structuredContentLength: structuredContentLength,
                             cancellationToken: cancellationToken);
                     }
 
@@ -2817,7 +2843,7 @@ internal async Task<Stream> OpenWriteInternal(
                     immutabilityPolicy: default,
                     legalHold: default,
                     progressHandler: default,
-                    transferValidationOverride: default,
+                    transferValidationOverride: new() { ChecksumAlgorithm = StorageChecksumAlgorithm.None },
                     operationName: default,
                     async: async,
                     cancellationToken: cancellationToken)
diff --git a/sdk/storage/Azure.Storage.Common/tests/Shared/TransferValidationTestBase.cs b/sdk/storage/Azure.Storage.Common/tests/Shared/TransferValidationTestBase.cs
index 05918941c9309..eda16484d7b19 100644
--- a/sdk/storage/Azure.Storage.Common/tests/Shared/TransferValidationTestBase.cs
+++ b/sdk/storage/Azure.Storage.Common/tests/Shared/TransferValidationTestBase.cs
@@ -5,6 +5,7 @@
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
+using System.Security.Cryptography;
 using System.Threading.Tasks;
 using Azure.Core;
 using Azure.Core.Pipeline;
@@ -1020,8 +1021,14 @@ public virtual async Task ParallelUploadOneShotSuccessfulHashComputation(Storage
             };
 
             // make pipeline assertion for checking checksum was present on upload
-            var checksumPipelineAssertion = new AssertMessageContentsPolicy(
-                checkRequest: GetRequestChecksumHeaderAssertion(algorithm, isChecksumExpected: ParallelUploadIsChecksumExpected));
+#if BlobSDK
+            var assertion = algorithm.ResolveAuto() == StorageChecksumAlgorithm.StorageCrc64
+                ? GetRequestStructuredMessageAssertion(StructuredMessage.Flags.StorageCrc64, ParallelUploadIsChecksumExpected, dataLength)
+                : GetRequestChecksumHeaderAssertion(algorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#else
+            var assertion = GetRequestChecksumHeaderAssertion(algorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#endif
+            var checksumPipelineAssertion = new AssertMessageContentsPolicy(checkRequest: assertion);
             var clientOptions = ClientBuilder.GetOptions();
             clientOptions.AddPolicy(checksumPipelineAssertion, HttpPipelinePosition.PerCall);
 
@@ -1108,8 +1115,14 @@ public virtual async Task ParallelUploadUsesDefaultClientValidationOptions(
                 };
 
             // make pipeline assertion for checking checksum was present on upload
-            var checksumPipelineAssertion = new AssertMessageContentsPolicy(checkRequest: GetRequestChecksumHeaderAssertion(
-                clientAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected));
+#if BlobSDK
+            var assertion = clientAlgorithm.ResolveAuto() == StorageChecksumAlgorithm.StorageCrc64 && !split
+                ? GetRequestStructuredMessageAssertion(StructuredMessage.Flags.StorageCrc64, ParallelUploadIsChecksumExpected, dataLength)
+                : GetRequestChecksumHeaderAssertion(clientAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#else
+            var assertion = GetRequestChecksumHeaderAssertion(clientAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#endif
+            var checksumPipelineAssertion = new AssertMessageContentsPolicy(checkRequest: assertion);
             var clientOptions = ClientBuilder.GetOptions();
             clientOptions.AddPolicy(checksumPipelineAssertion, HttpPipelinePosition.PerCall);
 
@@ -1160,8 +1173,14 @@ public virtual async Task ParallelUploadOverwritesDefaultClientValidationOptions
               };
 
             // make pipeline assertion for checking checksum was present on upload
-            var checksumPipelineAssertion = new AssertMessageContentsPolicy(checkRequest: GetRequestChecksumHeaderAssertion(
-                overrideAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected));
+#if BlobSDK
+            var assertion = overrideAlgorithm.ResolveAuto() == StorageChecksumAlgorithm.StorageCrc64 && !split
+                ? GetRequestStructuredMessageAssertion(StructuredMessage.Flags.StorageCrc64, ParallelUploadIsChecksumExpected, dataLength)
+                : GetRequestChecksumHeaderAssertion(overrideAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#else
+            var assertion = GetRequestChecksumHeaderAssertion(overrideAlgorithm, isChecksumExpected: ParallelUploadIsChecksumExpected);
+#endif
+            var checksumPipelineAssertion = new AssertMessageContentsPolicy(checkRequest: assertion);
             var clientOptions = ClientBuilder.GetOptions();
             clientOptions.AddPolicy(checksumPipelineAssertion, HttpPipelinePosition.PerCall);