diff --git a/cmd/copy.go b/cmd/copy.go
index 1dc1cc0b3..24525e28d 100644
--- a/cmd/copy.go
+++ b/cmd/copy.go
@@ -1607,6 +1607,11 @@ func (cca *CookedCopyCmdArgs) processCopyJobPartOrders() (err error) {
 		cca.StripTopDir = true
 	}
 
+	// TODO: Remove this check when FileBlob w/ File OAuth works.
+	if cca.FromTo.IsS2S() && cca.FromTo.From() == common.ELocation.File() && srcCredInfo.CredentialType.IsAzureOAuth() && cca.FromTo.To() != common.ELocation.File() {
+		return fmt.Errorf("S2S copy from Azure File authenticated with Azure AD to Blob/BlobFS is not supported")
+	}
+
 	switch {
 	case cca.FromTo.IsUpload(), cca.FromTo.IsDownload(), cca.FromTo.IsS2S():
 		// Execute a standard copy command
diff --git a/cmd/sync.go b/cmd/sync.go
index e98891384..50923c74c 100644
--- a/cmd/sync.go
+++ b/cmd/sync.go
@@ -705,6 +705,11 @@ func (cca *cookedSyncCmdArgs) process() (err error) {
 		}
 	}
 
+	// TODO: Remove this check when FileBlob w/ File OAuth works.
+	if cca.fromTo.IsS2S() && cca.fromTo.From() == common.ELocation.File() && srcCredInfo.CredentialType.IsAzureOAuth() && cca.fromTo.To() != common.ELocation.File() {
+		return fmt.Errorf("S2S sync from Azure File authenticated with Azure AD to Blob/BlobFS is not supported")
+	}
+
 	enumerator, err := cca.initEnumerator(ctx)
 	if err != nil {
 		return err
diff --git a/e2etest/newe2e_resource_managers_file.go b/e2etest/newe2e_resource_managers_file.go
index ba7bbd4e7..7d235f203 100644
--- a/e2etest/newe2e_resource_managers_file.go
+++ b/e2etest/newe2e_resource_managers_file.go
@@ -54,8 +54,7 @@ func (s *FileServiceResourceManager) DefaultAuthType() ExplicitCredentialTypes {
 }
 
 func (s *FileServiceResourceManager) ValidAuthTypes() ExplicitCredentialTypes {
-	// OAuth isn't supported *quite yet* in azcopy!
-	return EExplicitCredentialType.With(EExplicitCredentialType.SASToken())
+	return EExplicitCredentialType.With(EExplicitCredentialType.SASToken(), EExplicitCredentialType.OAuth())
 }
 
 func (s *FileServiceResourceManager) WithSpecificAuthType(cred ExplicitCredentialTypes, a Asserter, opts ...CreateAzCopyTargetOptions) AzCopyTarget {
diff --git a/e2etest/newe2e_task_resourcemanagement.go b/e2etest/newe2e_task_resourcemanagement.go
index 4e1965679..0154f717b 100644
--- a/e2etest/newe2e_task_resourcemanagement.go
+++ b/e2etest/newe2e_task_resourcemanagement.go
@@ -6,6 +6,7 @@ import (
 	"github.com/Azure/azure-storage-azcopy/v10/cmd"
 	"github.com/Azure/azure-storage-azcopy/v10/common"
 	"io"
+	"strings"
 )
 
 // ResourceTracker tracks resources
@@ -216,3 +217,15 @@ func ValidateListOutput(a Asserter, stdout AzCopyStdout, expectedObjects map[AzC
 			return KVPair[AzCopyOutputKey, cmd.AzCopyListObject]{Key: AzCopyOutputKey{Path: obj.Path, VersionId: obj.VersionId}, Value: obj}
 		}}, o...)
 }
+
+func ValidateErrorOutput(a Asserter, stdout AzCopyStdout, errorMsg string) {
+	if dryrunner, ok := a.(DryrunAsserter); ok && dryrunner.Dryrun() {
+		return
+	}
+	for _, line := range stdout.(*AzCopyRawStdout).RawOutput {
+		if strings.Contains(line, errorMsg) {
+			return
+		}
+	}
+	a.Error("expected error message not found in azcopy output")
+}
diff --git a/e2etest/newe2e_task_runazcopy.go b/e2etest/newe2e_task_runazcopy.go
index 3931e0649..0efa4eaf5 100644
--- a/e2etest/newe2e_task_runazcopy.go
+++ b/e2etest/newe2e_task_runazcopy.go
@@ -313,7 +313,7 @@ func RunAzCopy(a ScenarioAsserter, commandSpec AzCopyCommand) (AzCopyStdout, *Az
 	}
 
 	err = command.Wait()
-	a.Assert("wait for finalize", IsNil{}, err)
+	a.Assert("wait for finalize", common.Iff[Assertion](commandSpec.ShouldFail, Not{IsNil{}}, IsNil{}), err)
 	a.Assert("expected exit code",
 		common.Iff[Assertion](commandSpec.ShouldFail, Not{Equal{}}, Equal{}),
 		0, command.ProcessState.ExitCode())
diff --git a/e2etest/zt_newe2e_file_oauth_test.go b/e2etest/zt_newe2e_file_oauth_test.go
new file mode 100644
index 000000000..95c1de0c7
--- /dev/null
+++ b/e2etest/zt_newe2e_file_oauth_test.go
@@ -0,0 +1,39 @@
+package e2etest
+
+import (
+	"fmt"
+	"github.com/Azure/azure-storage-azcopy/v10/common"
+)
+
+func init() {
+	suiteManager.RegisterSuite(&FileOAuthTestSuite{})
+}
+
+type FileOAuthTestSuite struct{}
+
+func (s *FileOAuthTestSuite) Scenario_FileBlobOAuthError(svm *ScenarioVariationManager) {
+	azCopyVerb := ResolveVariation(svm, []AzCopyVerb{AzCopyVerbCopy, AzCopyVerbSync}) // Calculate verb early to create the destination object early
+
+	srcContainer := CreateResource[ContainerResourceManager](svm, GetRootResource(svm, common.ELocation.File()), ResourceDefinitionContainer{})
+	dstContainer := CreateResource[ContainerResourceManager](svm, GetRootResource(svm, common.ELocation.Blob()), ResourceDefinitionContainer{})
+
+	dstAuth := ResolveVariation(svm, []ExplicitCredentialTypes{EExplicitCredentialType.SASToken(), EExplicitCredentialType.OAuth()})
+
+	stdout, _ := RunAzCopy(
+		svm,
+		AzCopyCommand{
+			Verb: azCopyVerb,
+			Targets: []ResourceManager{
+				TryApplySpecificAuthType(srcContainer, EExplicitCredentialType.OAuth(), svm, CreateAzCopyTargetOptions{}),
+				TryApplySpecificAuthType(dstContainer, dstAuth, svm, CreateAzCopyTargetOptions{}),
+			},
+			Flags: CopyFlags{
+				CopySyncCommonFlags: CopySyncCommonFlags{
+					Recursive: pointerTo(true),
+				},
+			},
+			ShouldFail: true,
+		})
+
+	ValidateErrorOutput(svm, stdout, fmt.Sprintf("S2S %s from Azure File authenticated with Azure AD to Blob/BlobFS is not supported", azCopyVerb))
+}