diff --git a/README.md b/README.md
index bf46c626c..d82150016 100644
--- a/README.md
+++ b/README.md
@@ -939,10 +939,10 @@ SOFTWARE.
 [vscode-armhf-shield]: https://img.shields.io/badge/armhf-no-red.svg
 [vscode-armv7-shield]: https://img.shields.io/badge/armv7-no-red.svg
 [vscode-i386-shield]: https://img.shields.io/badge/i386-no-red.svg
-[addon-tailscale]: https://github.com/hassio-addons/addon-tailscale/tree/07fa745
-[addon-doc-tailscale]: https://github.com/hassio-addons/addon-tailscale/blob/07fa745/README.md
+[addon-tailscale]: https://github.com/hassio-addons/addon-tailscale/tree/f27d247
+[addon-doc-tailscale]: https://github.com/hassio-addons/addon-tailscale/blob/f27d247/README.md
 [tailscale-issue]: https://github.com/hassio-addons/addon-tailscale/issues
-[tailscale-version-shield]: https://img.shields.io/badge/version-07fa745-blue.svg
+[tailscale-version-shield]: https://img.shields.io/badge/version-f27d247-blue.svg
 [tailscale-aarch64-shield]: https://img.shields.io/badge/aarch64-yes-green.svg
 [tailscale-amd64-shield]: https://img.shields.io/badge/amd64-yes-green.svg
 [tailscale-armhf-shield]: https://img.shields.io/badge/armhf-yes-green.svg
diff --git a/tailscale/CHANGELOG.md b/tailscale/CHANGELOG.md
index 8da265dfe..6f002a289 100644
--- a/tailscale/CHANGELOG.md
+++ b/tailscale/CHANGELOG.md
@@ -1,4 +1,5 @@
 # Changelog since v0.11.1
+- ⬆️ Update tailscale/tailscale to v1.44.0 
 - ⬆️ Update Add-on base image to v14.0.2 
 - ⬆️ Update Add-on base image to v14.0.1 
 - ⬆️ Update alpine_3_18/nginx to v1.24.0-r6 (#208)
diff --git a/tailscale/README.md b/tailscale/README.md
index 919e206b0..d437ea2a9 100644
--- a/tailscale/README.md
+++ b/tailscale/README.md
@@ -48,5 +48,5 @@ If you are more interested in stable releases of our add-ons:
 [patreon-shield]: https://frenck.dev/wp-content/uploads/2019/12/patreon.png
 [patreon]: https://www.patreon.com/frenck
 [project-stage-shield]: https://img.shields.io/badge/project%20stage-experimental-yellow.svg
-[release-shield]: https://img.shields.io/badge/version-07fa745-blue.svg
-[release]: https://github.com/hassio-addons/addon-tailscale/tree/07fa745
\ No newline at end of file
+[release-shield]: https://img.shields.io/badge/version-f27d247-blue.svg
+[release]: https://github.com/hassio-addons/addon-tailscale/tree/f27d247
\ No newline at end of file
diff --git a/tailscale/config.yaml b/tailscale/config.yaml
index 5c0f88e76..365bc66d4 100644
--- a/tailscale/config.yaml
+++ b/tailscale/config.yaml
@@ -1,5 +1,5 @@
 name: Tailscale
-version: 07fa745
+version: f27d247
 slug: tailscale
 description: Zero config VPN for building secure networks
 url: https://github.com/hassio-addons/addon-tailscale