diff --git a/pkg/cmd/release/upload/upload.go b/pkg/cmd/release/upload/upload.go
index b3af37c4a..12cba4542 100644
--- a/pkg/cmd/release/upload/upload.go
+++ b/pkg/cmd/release/upload/upload.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"fmt"
 	"net/http"
+	"regexp"
 	"strings"
 
 	"github.com/MakeNowJust/heredoc"
@@ -93,8 +94,9 @@ func uploadRun(opts *UploadOptions) error {
 
 	var existingNames []string
 	for _, a := range opts.Assets {
+		sanitizedFileName := sanitizeFileName(a.Name)
 		for _, ea := range release.Assets {
-			if ea.Name == a.Name {
+			if ea.Name == sanitizedFileName {
 				a.ExistingURL = ea.APIURL
 				existingNames = append(existingNames, ea.Name)
 				break
@@ -122,3 +124,30 @@ func uploadRun(opts *UploadOptions) error {
 
 	return nil
 }
+
+// this method attempts to mimic the same functionality on the client that the platform does on
+// uploaded assets in order to allow the --clobber logic work correctly, since that feature is
+// one that only exists in the client
+func sanitizeFileName(name string) string {
+	value := text.RemoveDiacritics(name)
+	// Stripped all non-ascii characters, provide default name.
+	if strings.HasPrefix(value, ".") {
+		value = "default" + value
+	}
+
+	// Replace special characters with the separator
+	value = regexp.MustCompile(`(?i)[^a-z0-9\-_\+@]+`).ReplaceAllLiteralString(value, ".")
+
+	// No more than one of the separator in a row.
+	value = regexp.MustCompile(`\.{2,}`).ReplaceAllLiteralString(value, ".")
+
+	// Remove leading/trailing separator.
+	value = strings.Trim(value, ".")
+
+	// Just file extension left, add default name.
+	if name != value && !strings.Contains(value, ".") {
+		value = "default." + value
+	}
+
+	return value
+}
diff --git a/pkg/cmd/release/upload/upload_test.go b/pkg/cmd/release/upload/upload_test.go
new file mode 100644
index 000000000..7a85c82a3
--- /dev/null
+++ b/pkg/cmd/release/upload/upload_test.go
@@ -0,0 +1,52 @@
+package upload
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func Test_SanitizeFileName(t *testing.T) {
+	tests := []struct {
+		name     string
+		expected string
+	}{
+		{
+			name:     "foo",
+			expected: "foo",
+		},
+		{
+			name:     "foo bar",
+			expected: "foo.bar",
+		},
+		{
+			name:     ".foo",
+			expected: "default.foo",
+		},
+		{
+			name:     "Foo bar",
+			expected: "Foo.bar",
+		},
+		{
+			name:     "Hello, दुनिया",
+			expected: "default.Hello",
+		},
+		{
+			name:     "this+has+plusses.jpg",
+			expected: "this+has+plusses.jpg",
+		},
+		{
+			name:     "this@has@at@signs.jpg",
+			expected: "this@has@at@signs.jpg",
+		},
+		{
+			name:     "façade.exposé",
+			expected: "facade.expose",
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			assert.Equal(t, tt.expected, sanitizeFileName(tt.name))
+		})
+	}
+}