diff --git a/changes/5138-mdm-migration-err b/changes/5138-mdm-migration-err
new file mode 100644
index 0000000000..9db0aa201f
--- /dev/null
+++ b/changes/5138-mdm-migration-err
@@ -0,0 +1,2 @@
+- Fixes issue where a bad request response from a 3rd party MDM solution would result in a 500 error
+  in Fleet during MDM migration.
diff --git a/server/service/integration_mdm_test.go b/server/service/integration_mdm_test.go
index 495a0a1e15..afcf2ce089 100644
--- a/server/service/integration_mdm_test.go
+++ b/server/service/integration_mdm_test.go
@@ -6196,6 +6196,75 @@ func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhook() {
 	require.False(t, webhookCalled)
 }
 
+func (s *integrationMDMTestSuite) TestMigrateMDMDeviceWebhookErrors() {
+	t := s.T()
+
+	h := createHostAndDeviceToken(t, s.ds, "good-token")
+
+	var webhookCalled bool
+	webhookSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		webhookCalled = true
+		w.WriteHeader(http.StatusBadRequest)
+	}))
+	defer webhookSrv.Close()
+
+	// patch app config with webhook url
+	acResp := fleet.AppConfig{}
+	s.DoJSON("PATCH", "/api/latest/fleet/config", json.RawMessage(fmt.Sprintf(`{
+		"mdm": {
+			"macos_migration": {
+				"enable": true,
+				"mode": "voluntary",
+				"webhook_url": "%s/test_mdm_migration"
+			}
+		}
+	}`, webhookSrv.URL)), http.StatusOK, &acResp)
+	require.True(t, acResp.MDM.MacOSMigration.Enable)
+
+	isServer, enrolled, installedFromDEP := true, true, true
+	mdmName := "ExampleMDM"
+	mdmURL := "https://mdm.example.com"
+
+	// host is enrolled to a third-party MDM but hasn't been assigned in
+	// ABM yet, so migration is not allowed
+	require.NoError(t, s.ds.SetOrUpdateMDMData(context.Background(), h.ID, !isServer, enrolled, mdmURL, installedFromDEP, mdmName, ""))
+	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.False(t, webhookCalled)
+
+	// simulate that the device is assigned to Fleet in ABM
+	s.mockDEPResponse(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+		switch r.URL.Path {
+		case "/session":
+			_, _ = w.Write([]byte(`{"auth_session_token": "xyz"}`))
+		case "/profile":
+			encoder := json.NewEncoder(w)
+			err := encoder.Encode(godep.ProfileResponse{ProfileUUID: "abc"})
+			require.NoError(t, err)
+		case "/server/devices", "/devices/sync":
+			encoder := json.NewEncoder(w)
+			err := encoder.Encode(godep.DeviceResponse{
+				Devices: []godep.Device{
+					{
+						SerialNumber: h.HardwareSerial,
+						Model:        "Mac Mini",
+						OS:           "osx",
+						OpType:       "added",
+					},
+				},
+			})
+			require.NoError(t, err)
+		}
+	}))
+	s.runDEPSchedule()
+
+	// hosts meets all requirements, webhook is run but returns an error, server should respond with
+	// the same status code
+	require.False(t, webhookCalled)
+	s.Do("POST", fmt.Sprintf("/api/v1/fleet/device/%s/migrate_mdm", "good-token"), nil, http.StatusBadRequest)
+	require.True(t, webhookCalled)
+}
+
 func (s *integrationMDMTestSuite) TestMDMMacOSSetup() {
 	t := s.T()
 
diff --git a/server/utils.go b/server/utils.go
index 76643ee4fd..4d8edbae81 100644
--- a/server/utils.go
+++ b/server/utils.go
@@ -37,6 +37,22 @@ func httpSuccessStatus(statusCode int) bool {
 	return statusCode >= 200 && statusCode <= 299
 }
 
+// errWithStatus is an error with a particular status code.
+type errWithStatus struct {
+	err        string
+	statusCode int
+}
+
+// Error implements the error interface
+func (e *errWithStatus) Error() string {
+	return e.err
+}
+
+// StatusCode implements the StatusCoder interface for returning custom status codes.
+func (e *errWithStatus) StatusCode() int {
+	return e.statusCode
+}
+
 func PostJSONWithTimeout(ctx context.Context, url string, v interface{}) error {
 	jsonBytes, err := json.Marshal(v)
 	if err != nil {
@@ -59,7 +75,7 @@ func PostJSONWithTimeout(ctx context.Context, url string, v interface{}) error {
 
 	if !httpSuccessStatus(resp.StatusCode) {
 		body, _ := io.ReadAll(resp.Body)
-		return fmt.Errorf("error posting to %s: %d. %s", MaskSecretURLParams(url), resp.StatusCode, string(body))
+		return &errWithStatus{err: fmt.Sprintf("error posting to %s: %d. %s", MaskSecretURLParams(url), resp.StatusCode, string(body)), statusCode: resp.StatusCode}
 	}
 
 	return nil
diff --git a/website/api/controllers/webhooks/receive-from-customer-fleet-instance.js b/website/api/controllers/webhooks/receive-from-customer-fleet-instance.js
index 92b808557a..98ee042d2d 100644
--- a/website/api/controllers/webhooks/receive-from-customer-fleet-instance.js
+++ b/website/api/controllers/webhooks/receive-from-customer-fleet-instance.js
@@ -41,6 +41,10 @@ module.exports = {
     unauthorized: {
       responseType: 'unauthorized',
       description: 'This webhook request could not be verified.',
+    },
+    badRequest: {
+      responseType: 'badRequest',
+      description: 'Invalid MDM migration request.'
     }
   },
 
@@ -102,7 +106,7 @@ module.exports = {
       if(err.raw.statusCode === 404){
         return new Error(`When sending a request to unenroll a host from a Workspace One instance (Host information: Serial number: ${host.hardware_serial}, id: ${host.id}, uuid: ${host.uuid}), the specified host was not found on the customer's Workspace One instance. Full error: ${err.stack}`);
       } else if(err.raw.statusCode === 400) {
-        return new Error(`When sending a request to unenroll a host from a Workspace One instance (Host information: Serial number: ${host.hardware_serial}, id: ${host.id}, uuid: ${host.uuid}), the Workspace One instance could not unenroll the specified host. Full error: ${err.stack}`);
+        return { badRequest: `When sending a request to unenroll a host from a Workspace One instance (Host information: Serial number: ${host.hardware_serial}, id: ${host.id}, uuid: ${host.uuid}), the Workspace One instance could not unenroll the specified host. Full error: ${err.stack}` };
       } else {
         return new Error(`When sending a request to unenroll a host from a Workspace One instance (Host information: Serial number: ${host.hardware_serial}, id: ${host.id}, uuid: ${host.uuid}), an error occured. Full error: ${err.stack}`);
       }