diff --git a/CHANGELOG.md b/CHANGELOG.md
index b81cca33116e..3776f0804ba8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,28 @@ Code v99.99.999
 
 ## Unreleased
 
+## [4.100.0](https://github.com/coder/code-server/releases/tag/v4.100.0) - 2025-05-12
+
+Code v1.100.0
+
+### Added
+
+- Trusted domains for links can now be set at run-time by configuring
+  `linkProtectionTrustedDomains` in the `lib/vscode/product.json` file or via
+  the `--link-protection-trusted-domains` flag.
+
+### Changed
+
+- Update to Code 1.100.0.
+- Disable extension signature verification, which previously was skipped by
+  default (the package used for verification is not available to OSS builds of
+  VS Code) but now reportedly throws hard errors making it impossible to install
+  extensions.
+
+### Fixed
+
+- Flags with repeatable options now work via the config file.
+
 ## [4.99.4](https://github.com/coder/code-server/releases/tag/v4.99.4) - 2025-05-02
 
 Code v1.99.3
diff --git a/ci/helm-chart/Chart.yaml b/ci/helm-chart/Chart.yaml
index 63c9483a5026..f72c0d82d50e 100644
--- a/ci/helm-chart/Chart.yaml
+++ b/ci/helm-chart/Chart.yaml
@@ -15,9 +15,9 @@ type: application
 # This is the chart version. This version number should be incremented each time you make changes
 # to the chart and its templates, including the app version.
 # Versions are expected to follow Semantic Versioning (https://semver.org/)
-version: 3.26.4
+version: 3.27.0
 
 # This is the version number of the application being deployed. This version number should be
 # incremented each time you make changes to the application. Versions are not expected to
 # follow Semantic Versioning. They should reflect the version the application is using.
-appVersion: 4.99.4
+appVersion: 4.100.0
diff --git a/ci/helm-chart/values.yaml b/ci/helm-chart/values.yaml
index 3790acc7e006..6a78a7fc8610 100644
--- a/ci/helm-chart/values.yaml
+++ b/ci/helm-chart/values.yaml
@@ -6,7 +6,7 @@ replicaCount: 1
 
 image:
   repository: codercom/code-server
-  tag: '4.99.4'
+  tag: '4.100.0'
   pullPolicy: Always
 
 # Specifies one or more secrets to be used when pulling images from a
diff --git a/lib/vscode b/lib/vscode
index 19e0f9e681ec..91fa95bccb02 160000
--- a/lib/vscode
+++ b/lib/vscode
@@ -1 +1 @@
-Subproject commit 19e0f9e681ecb8e5c09d8784acaa601316ca4571
+Subproject commit 91fa95bccb027ece6a968589bb1d662fa9c8e170