diff --git a/server/mdm/apple/itunes/api.go b/server/mdm/apple/itunes/api.go
index fafac6a82f..f81fe878eb 100644
--- a/server/mdm/apple/itunes/api.go
+++ b/server/mdm/apple/itunes/api.go
@@ -12,6 +12,7 @@ import (
 	"time"
 
 	"github.com/fleetdm/fleet/v4/pkg/fleethttp"
+	"github.com/fleetdm/fleet/v4/pkg/retry"
 )
 
 type AssetMetadata struct {
@@ -86,6 +87,16 @@ func do[T any](req *http.Request, dest *T) error {
 		if len(limitedBody) > 1000 {
 			limitedBody = limitedBody[:1000]
 		}
+
+		if resp.StatusCode >= http.StatusInternalServerError {
+			return retry.Do(
+				func() error { return do(req, dest) },
+				retry.WithInterval(1*time.Second),
+				retry.WithMaxAttempts(4),
+			)
+
+		}
+
 		return fmt.Errorf("calling Apple iTunes endpoint failed with status %d: %s", resp.StatusCode, string(limitedBody))
 	}
 
diff --git a/server/mdm/apple/itunes/api_test.go b/server/mdm/apple/itunes/api_test.go
index a43031fcea..bec950ff6f 100644
--- a/server/mdm/apple/itunes/api_test.go
+++ b/server/mdm/apple/itunes/api_test.go
@@ -1,8 +1,11 @@
 package itunes
 
 import (
+	"net/http"
+	"net/http/httptest"
 	"os"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/require"
 )
@@ -19,3 +22,69 @@ func TestGetBaseURL(t *testing.T) {
 		require.Equal(t, customURL, getBaseURL())
 	})
 }
+
+func setupFakeServer(t *testing.T, handler http.HandlerFunc) {
+	server := httptest.NewServer(handler)
+	os.Setenv("FLEET_DEV_ITUNES_URL", server.URL)
+	t.Cleanup(server.Close)
+}
+
+func TestDoRetries(t *testing.T) {
+	tests := []struct {
+		name      string
+		handler   http.HandlerFunc
+		wantCalls int
+		wantErr   bool
+	}{
+		{
+			name: "success status code",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusOK)
+				_, err := w.Write([]byte("{}"))
+				require.NoError(t, err)
+			},
+			wantCalls: 1,
+			wantErr:   true,
+		},
+		{
+			name: "bad requests",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusBadRequest)
+				_, err := w.Write([]byte("{}"))
+				require.NoError(t, err)
+			},
+			wantCalls: 1,
+			wantErr:   true,
+		},
+		{
+			name: "500 requests retries",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusServiceUnavailable)
+				_, err := w.Write([]byte("{}"))
+				require.NoError(t, err)
+			},
+			wantCalls: 4,
+			wantErr:   false,
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			var calls int
+			setupFakeServer(t, func(w http.ResponseWriter, r *http.Request) {
+				calls++
+				if calls < tt.wantCalls {
+					tt.handler(w, r)
+					return
+				}
+			})
+
+			start := time.Now()
+			req, err := http.NewRequest(http.MethodGet, os.Getenv("FLEET_DEV_ITUNES_URL"), nil)
+			require.NoError(t, err)
+			err = do[any](req, nil)
+			require.NoError(t, err)
+			require.Equal(t, tt.wantCalls, calls)
+			require.WithinRange(t, time.Now(), start, start.Add(time.Duration(tt.wantCalls)*time.Second))
+		})
+	}
+}