diff --git a/.gitignore b/.gitignore
index d64770ac3c..0059f2561c 100644
--- a/.gitignore
+++ b/.gitignore
@@ -65,6 +65,7 @@ desktop.app.tar.gz
 osqueryd.app.tar.gz
 desktop.tar.gz
 nudge.app.tar.gz
+swiftDialog.app.tar.gz
 
 # residual files when running the cpe command
 cmd/cpe/etagenv
diff --git a/Makefile b/Makefile
index bc636adf3e..df46760cfe 100644
--- a/Makefile
+++ b/Makefile
@@ -360,6 +360,24 @@ endif
 	tar czf $(out-path)/nudge.app.tar.gz -C $(TMP_DIR)/nudge_pkg_payload_expanded/ Nudge.app
 	rm -r $(TMP_DIR)
 
+# Generate swiftDialog.app.tar.gz bundle from the swiftDialog repo.
+#
+# Usage:
+# make swift-dialog-app-tar-gz version=2.1.0 build=4148 out-path=.
+swift-dialog-app-tar-gz:
+ifneq ($(shell uname), Darwin)
+	@echo "Makefile target swift-dialog-app-tar-gz is only supported on macOS"
+	@exit 1
+endif
+	$(eval TMP_DIR := $(shell mktemp -d))
+	curl -L https://github.com/bartreardon/swiftDialog/releases/download/v$(version)/dialog-$(version)-$(build).pkg --output $(TMP_DIR)/swiftDialog-$(version).pkg
+	pkgutil --expand $(TMP_DIR)/swiftDialog-$(version).pkg $(TMP_DIR)/swiftDialog_pkg_expanded
+	mkdir -p $(TMP_DIR)/swiftDialog_pkg_payload_expanded
+	tar xvf $(TMP_DIR)/swiftDialog_pkg_expanded/Payload --directory $(TMP_DIR)/swiftDialog_pkg_payload_expanded
+	$(TMP_DIR)/swiftDialog_pkg_payload_expanded/usr/local/bin/dialog --version
+	tar czf $(out-path)/swiftDialog.app.tar.gz -C $(TMP_DIR)/swiftDialog_pkg_payload_expanded/usr/local bin
+	rm -rf $(TMP_DIR)
+
 # Build and generate desktop.app.tar.gz bundle.
 #
 # Usage:
diff --git a/orbit/pkg/update/notifications.go b/orbit/pkg/update/notifications.go
index ce6a514ca9..9d15c76c05 100644
--- a/orbit/pkg/update/notifications.go
+++ b/orbit/pkg/update/notifications.go
@@ -44,6 +44,18 @@ func ApplyRenewEnrollmentProfileConfigFetcherMiddleware(fetcher OrbitConfigFetch
 // to renew the enrollment profile.
 func (h *RenewEnrollmentProfileConfigFetcher) GetConfig() (*fleet.OrbitConfig, error) {
 	cfg, err := h.Fetcher.GetConfig()
+
+	// TODO: download and use swiftDialog following the same patterns we
+	// use for Nudge.
+	//
+	// updaterHasTarget := h.UpdateRunner.HasRunnerOptTarget("swiftDialog")
+	// runnerHasLocalHash := h.UpdateRunner.HasLocalHash("swiftDialog")
+	// if !updaterHasTarget || !runnerHasLocalHash {
+	//         log.Info().Msg("refreshing the update runner config with swiftDialog targets and hashes")
+	//         log.Debug().Msgf("updater has target: %t, runner has local hash: %t", updaterHasTarget, runnerHasLocalHash)
+	//         return cfg, h.setTargetsAndHashes()
+	// }
+
 	if err == nil && cfg.Notifications.RenewEnrollmentProfile {
 		if h.cmdMu.TryLock() {
 			defer h.cmdMu.Unlock()
diff --git a/orbit/pkg/update/options.go b/orbit/pkg/update/options.go
index f93fbb40bd..c02a33f31f 100644
--- a/orbit/pkg/update/options.go
+++ b/orbit/pkg/update/options.go
@@ -88,4 +88,11 @@ var (
 		TargetFile:           "nudge.app.tar.gz",
 		ExtractedExecSubPath: []string{"Nudge.app", "Contents", "MacOS", "Nudge"},
 	}
+
+	SwiftDialogTarget = TargetInfo{
+		Platform:             "macos",
+		Channel:              "stable",
+		TargetFile:           "swiftDialog.app.tar.gz",
+		ExtractedExecSubPath: []string{"bin", "dialog"},
+	}
 )
diff --git a/tools/tuf/test/create_repository.sh b/tools/tuf/test/create_repository.sh
index 7fb1fe8667..e9ac7aab0e 100755
--- a/tools/tuf/test/create_repository.sh
+++ b/tools/tuf/test/create_repository.sh
@@ -25,6 +25,8 @@ fi
 
 SYSTEMS=${SYSTEMS:-macos linux windows}
 NUDGE_VERSION=stable
+SWIFT_DIALOG_MACOS_APP_VERSION=2.1.0
+SWIFT_DIALOG_MACOS_APP_BUILD_VERSION=4148
 
 if [[ -z "$OSQUERY_VERSION" ]]; then
     OSQUERY_VERSION=5.8.1
@@ -111,6 +113,20 @@ for system in $SYSTEMS; do
         rm nudge.app.tar.gz
     fi
 
+    # Add swiftDialog on macos (if enabled).
+    if [[ $system == "macos" && -n "$SWIFT_DIALOG" ]]; then
+	# For now we always make swiftDialog (until it's uploaded to our TUF repo)
+        make swift-dialog-app-tar-gz version=$SWIFT_DIALOG_MACOS_APP_VERSION build=$SWIFT_DIALOG_MACOS_APP_BUILD_VERSION out-path=.
+
+        ./build/fleetctl updates add \
+            --path $TUF_PATH \
+            --target swiftDialog.app.tar.gz \
+            --platform macos \
+            --name swiftDialog \
+            --version 42.0.0 -t 42.0 -t 42 -t stable
+        rm swiftDialog.app.tar.gz
+    fi
+
     # Add Fleet Desktop application on windows (if enabled).
     if [[ $system == "windows" && -n "$FLEET_DESKTOP" ]]; then
         FLEET_DESKTOP_VERSION=42.0.0 \