diff --git a/pkg/registry/client.go b/pkg/registry/client.go
index f2bfd13b4..d6a12d674 100644
--- a/pkg/registry/client.go
+++ b/pkg/registry/client.go
@@ -30,11 +30,13 @@ import (
 	"os"
 	"sort"
 	"strings"
+	"unicode/utf8"
 
 	"github.com/Masterminds/semver/v3"
 	"github.com/opencontainers/image-spec/specs-go"
 	ocispec "github.com/opencontainers/image-spec/specs-go/v1"
 	"oras.land/oras-go/v2"
+	"oras.land/oras-go/v2/content"
 	"oras.land/oras-go/v2/content/memory"
 	"oras.land/oras-go/v2/registry"
 	"oras.land/oras-go/v2/registry/remote"
@@ -719,6 +721,9 @@ func (c *Client) Push(data []byte, ref string, options ...PushOption) (*PushResu
 
 	manifestDescriptor, err = oras.ExtendedCopy(ctx, memoryStore, parsedRef.String(), repository, parsedRef.String(), oras.DefaultExtendedCopyOptions)
 	if err != nil {
+		if hasNonASCIIAnnotationValues(ociAnnotations) && errors.Is(err, content.ErrMismatchedDigest) {
+			return nil, fmt.Errorf("manifest digest mismatch while pushing; the registry may be rewriting non-ASCII OCI annotation values. Consider using ASCII-only metadata/annotations or a registry that preserves annotations: %w", err)
+		}
 		return nil, err
 	}
 
@@ -756,6 +761,24 @@ func (c *Client) Push(data []byte, ref string, options ...PushOption) (*PushResu
 	return result, err
 }
 
+func hasNonASCIIAnnotationValues(annotations map[string]string) bool {
+	for key, value := range annotations {
+		if containsNonASCII(key) || containsNonASCII(value) {
+			return true
+		}
+	}
+	return false
+}
+
+func containsNonASCII(value string) bool {
+	for i := 0; i < len(value); i++ {
+		if value[i] >= utf8.RuneSelf {
+			return true
+		}
+	}
+	return false
+}
+
 // PushOptProvData returns a function that sets the prov bytes setting on push
 func PushOptProvData(provData []byte) PushOption {
 	return func(operation *pushOperation) {
diff --git a/pkg/registry/client_test.go b/pkg/registry/client_test.go
index 702dfff69..da915a941 100644
--- a/pkg/registry/client_test.go
+++ b/pkg/registry/client_test.go
@@ -166,3 +166,54 @@ func TestWarnIfHostHasPath(t *testing.T) {
 		})
 	}
 }
+
+func TestHasNonASCIIAnnotationValues(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name        string
+		annotations map[string]string
+		want        bool
+	}{
+		{
+			name: "ascii only",
+			annotations: map[string]string{
+				"org.opencontainers.image.title": "chart",
+				"custom":                         "alpha-._:@/+ 123",
+			},
+			want: false,
+		},
+		{
+			name: "non-ascii value",
+			annotations: map[string]string{
+				"org.opencontainers.image.description": "Kröpke",
+			},
+			want: true,
+		},
+		{
+			name: "non-ascii key",
+			annotations: map[string]string{
+				"\uC124\uBA85": "chart",
+			},
+			want: true,
+		},
+		{
+			name: "emoji value",
+			annotations: map[string]string{
+				"note": "chart \U0001F600",
+			},
+			want: true,
+		},
+		{
+			name:        "empty map",
+			annotations: map[string]string{},
+			want:        false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			require.Equal(t, tt.want, hasNonASCIIAnnotationValues(tt.annotations))
+		})
+	}
+}