diff --git a/.github/workflows/_build_artifacts.yml b/.github/workflows/_build_artifacts.yml
index fa02fdaf3..d55d20a47 100644
--- a/.github/workflows/_build_artifacts.yml
+++ b/.github/workflows/_build_artifacts.yml
@@ -131,9 +131,9 @@ jobs:
         target: [x86_64-pc-windows-msvc]
         package: [firezone-headless-client]
         # mark:next-headless-version
-        release_name: [headless-client-1.4.3]
+        release_name: [headless-client-1.4.4]
         # mark:next-headless-version
-        version: [1.4.3]
+        version: [1.4.4]
     env:
       ARTIFACT_PATH: ${{ matrix.artifact }}_${{ matrix.version }}_${{ matrix.arch }}.exe
       RELEASE_NAME: ${{ matrix.release_name }}
@@ -215,9 +215,9 @@ jobs:
             artifact: firezone-client-headless-linux
             image_name: client
             # mark:next-headless-version
-            release_name: headless-client-1.4.3
+            release_name: headless-client-1.4.4
             # mark:next-headless-version
-            version: 1.4.3
+            version: 1.4.4
           - package: firezone-relay
             artifact: firezone-relay
             image_name: relay
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 4c10cd46c..050081d56 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -50,7 +50,7 @@ jobs:
           - release_name: gateway-1.4.4
             config_name: release-drafter-gateway.yml
           # mark:next-headless-version
-          - release_name: headless-client-1.4.3
+          - release_name: headless-client-1.4.4
             config_name: release-drafter-headless-client.yml
 
     steps:
diff --git a/.github/workflows/publish.yml b/.github/workflows/publish.yml
index aa386b85d..eb53330c0 100644
--- a/.github/workflows/publish.yml
+++ b/.github/workflows/publish.yml
@@ -42,7 +42,7 @@ jobs:
           elif [[ "${{ github.event.release.name }}" =~ headless* ]]; then
             ARTIFACT=client
             # mark:next-headless-version
-            VERSION="1.4.3"
+            VERSION="1.4.4"
           else
             echo "Shouldn't have gotten here. Exiting."
             exit 1
diff --git a/rust/Cargo.lock b/rust/Cargo.lock
index 30f8dfd66..f95a368b5 100644
--- a/rust/Cargo.lock
+++ b/rust/Cargo.lock
@@ -2108,7 +2108,7 @@ dependencies = [
 
 [[package]]
 name = "firezone-headless-client"
-version = "1.4.3"
+version = "1.4.4"
 dependencies = [
  "anyhow",
  "atomicwrites",
diff --git a/rust/headless-client/Cargo.toml b/rust/headless-client/Cargo.toml
index 2930c6881..e0c75b059 100644
--- a/rust/headless-client/Cargo.toml
+++ b/rust/headless-client/Cargo.toml
@@ -1,7 +1,7 @@
 [package]
 name = "firezone-headless-client"
 # mark:next-headless-version
-version = "1.4.3"
+version = "1.4.4"
 edition = { workspace = true }
 authors = ["Firezone, Inc."]
 license = { workspace = true }
diff --git a/scripts/bump-versions.sh b/scripts/bump-versions.sh
index 278e66fc4..cba81caf9 100755
--- a/scripts/bump-versions.sh
+++ b/scripts/bump-versions.sh
@@ -131,8 +131,8 @@ function gui() {
 # 4. Commit the changes and open a PR. Ensure the Changelog is correctly
 #    updated with the changes.
 function headless() {
-    current_headless_version="1.4.2"
-    next_headless_version="1.4.3"
+    current_headless_version="1.4.3"
+    next_headless_version="1.4.4"
 
     find website -type f -name "redirects.js" -exec sed "${SEDARG[@]}" -e '/mark:current-headless-version/{n;s/[0-9]\{1,\}\.[0-9]\{1,\}\.[0-9]\{1,\}/'"${current_headless_version}"'/g;}' {} \;
     find website -type f -name "route.ts" -exec sed "${SEDARG[@]}" -e '/mark:current-headless-version/{n;s/[0-9]\{1,\}\.[0-9]\{1,\}\.[0-9]\{1,\}/'"${current_headless_version}"'/g;}' {} \;
diff --git a/website/redirects.js b/website/redirects.js
index 570ffd4eb..6e7f22908 100644
--- a/website/redirects.js
+++ b/website/redirects.js
@@ -46,7 +46,7 @@ module.exports = [
     source: "/dl/firezone-client-headless-windows/latest/x86_64",
     destination:
       // mark:current-headless-version
-      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.2/firezone-client-headless-windows_1.4.2_x86_64.exe",
+      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.3/firezone-client-headless-windows_1.4.3_x86_64.exe",
     permanent: false,
   },
   /*
@@ -72,21 +72,21 @@ module.exports = [
     source: "/dl/firezone-client-headless-linux/latest/x86_64",
     destination:
       // mark:current-headless-version
-      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.2/firezone-client-headless-linux_1.4.2_x86_64",
+      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.3/firezone-client-headless-linux_1.4.3_x86_64",
     permanent: false,
   },
   {
     source: "/dl/firezone-client-headless-linux/latest/aarch64",
     destination:
       // mark:current-headless-version
-      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.2/firezone-client-headless-linux_1.4.2_aarch64",
+      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.3/firezone-client-headless-linux_1.4.3_aarch64",
     permanent: false,
   },
   {
     source: "/dl/firezone-client-headless-linux/latest/armv7",
     destination:
       // mark:current-headless-version
-      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.2/firezone-client-headless-linux_1.4.2_armv7",
+      "https://www.github.com/firezone/firezone/releases/download/headless-client-1.4.3/firezone-client-headless-linux_1.4.3_armv7",
     permanent: false,
   },
   /*
diff --git a/website/src/app/api/releases/route.ts b/website/src/app/api/releases/route.ts
index 7c66ef741..697b6a16d 100644
--- a/website/src/app/api/releases/route.ts
+++ b/website/src/app/api/releases/route.ts
@@ -11,7 +11,7 @@ export async function GET(_req: NextRequest) {
     // mark:current-gui-version
     gui: "1.4.4",
     // mark:current-headless-version
-    headless: "1.4.2",
+    headless: "1.4.3",
     // mark:current-gateway-version
     gateway: "1.4.3",
   };
diff --git a/website/src/components/Changelog/Headless.tsx b/website/src/components/Changelog/Headless.tsx
index 56a62da04..da12a91ab 100644
--- a/website/src/components/Changelog/Headless.tsx
+++ b/website/src/components/Changelog/Headless.tsx
@@ -9,7 +9,8 @@ export default function Headless({ os }: { os: OS }) {
   return (
     <Entries downloadLinks={downloadLinks(os)} title={title(os)}>
       {/* When you cut a release, remove any solved issues from the "known issues" lists over in `client-apps`. This must not be done when the issue's PR merges. */}
-      <Unreleased>
+      <Unreleased></Unreleased>
+      <Entry version="1.4.3" date={new Date("2025-02-11")}>
         <ChangeItem pull="8055">
           Hides the <code>--check</code> and <code>--exit</code> CLI options
           from the help output. These are only used internally.
@@ -20,7 +21,7 @@ export default function Headless({ os }: { os: OS }) {
             on systems with a disabled IPv6 stack.
           </ChangeItem>
         )}
-      </Unreleased>
+      </Entry>
       <Entry version="1.4.2" date={new Date("2025-02-10")}>
         <ChangeItem pull="8041">
           Publishes the headless client for Windows.