diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index 4ee0385c521932..df755d3e1680e2 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -1,41 +1,38 @@
 {
-    "name": "gitpod",
-    "build": {
-        "context": "..",
-        "dockerfile": "./Dockerfile"
-    },
-    "workspaceMount": "source=${localWorkspaceFolder},target=/workspace/gitpod,type=bind",
-    "workspaceFolder": "/workspace/gitpod/",
-    "postCreateCommand": "dev/install-dependencies.sh",
-    "mounts": [
-        "source=/usr/local/gitpod/config/,target=/usr/local/gitpod/config/,type=bind"
-    ],
-    "remoteEnv": {
-        "GIT_EDITOR": "code --wait",
-        "KUBE_EDITOR": "code --wait"
-    },
-    "features": {
-        "ghcr.io/devcontainers/features/docker-in-docker:2": {
-            "installDockerComposeSwitch": false
-        }
-    },
-    "customizations": {
-        "vscode": {
-            "extensions": [
-                "EditorConfig.EditorConfig",
-                "golang.go",
-                "hashicorp.terraform",
-                "ms-azuretools.vscode-docker",
-                "ms-kubernetes-tools.vscode-kubernetes-tools",
-                "stkb.rewrap",
-                "zxh404.vscode-proto3",
-                "matthewpi.caddyfile-support",
-                "timonwong.shellcheck",
-                "fwcd.kotlin",
-                "dbaeumer.vscode-eslint",
-                "esbenp.prettier-vscode",
-                "hbenl.vscode-mocha-test-adapter"
-            ]
-        }
+  "name": "gitpod",
+  "build": {
+    "context": "..",
+    "dockerfile": "./Dockerfile"
+  },
+  "features": {
+    "ghcr.io/devcontainers/features/docker-in-docker:2": {}
+  },
+  "workspaceFolder": "/workspace/gitpod",
+  "workspaceMount": "source=${localWorkspaceFolder},target=/workspace/gitpod,type=bind",
+  "mounts": [
+    "source=/usr/local/gitpod/config/,target=/usr/local/gitpod/config/,type=bind"
+  ],
+  "remoteEnv": {
+    "GIT_EDITOR": "code --wait",
+    "KUBE_EDITOR": "code --wait"
+  },
+  "customizations": {
+    "vscode": {
+      "extensions": [
+        "EditorConfig.EditorConfig",
+        "golang.go",
+        "hashicorp.terraform",
+        "ms-azuretools.vscode-docker",
+        "ms-kubernetes-tools.vscode-kubernetes-tools",
+        "stkb.rewrap",
+        "zxh404.vscode-proto3",
+        "matthewpi.caddyfile-support",
+        "timonwong.shellcheck",
+        "fwcd.kotlin",
+        "dbaeumer.vscode-eslint",
+        "esbenp.prettier-vscode",
+        "hbenl.vscode-mocha-test-adapter"
+      ]
     }
+  }
 }
diff --git a/.gitignore b/.gitignore
index c4cae571fe90df..6d36ce9ede3426 100644
--- a/.gitignore
+++ b/.gitignore
@@ -64,3 +64,6 @@ dump.rdb
 
 # Claude settings
 .claude/settings.local.json
+
+# Gitpod mcp-config.json
+.gitpod/mcp-config.json
diff --git a/.gitpod/automations.yaml b/.gitpod/automations.yaml
new file mode 100644
index 00000000000000..c29a9ed4021a67
--- /dev/null
+++ b/.gitpod/automations.yaml
@@ -0,0 +1,50 @@
+tasks:
+    installLocalAppCli:
+        command: |
+            leeway run components/local-app:install-cli
+            leeway run components/local-app:cli-completion
+            exit 0
+        name: 'Install `gitpod` CLI'
+        triggeredBy:
+            - postDevcontainerStart
+    configurePreview:
+        command: INSTALL_CONTEXT=true leeway run dev/preview:configure-workspace
+        dependsOn:
+            - installPreviewctl
+        name: 'Preview environment configuration'
+        triggeredBy:
+            - postDevcontainerStart
+    buildJava:
+        command: |
+            leeway exec --package components/supervisor-api/java:lib --package components/gitpod-protocol/java:lib -- ./gradlew build
+            leeway exec --package components/ide/jetbrains/backend-plugin:plugin-latest --package components/ide/jetbrains/gateway-plugin:publish-latest --parallel -- ./gradlew buildPlugin
+        name: 'Java: build with Gradle'
+    installPreviewctl:
+        command: leeway run dev/preview/previewctl:install
+        name: 'Preview environment configuration: init'
+    installInstallerDependencies:
+        command: |
+            (cd install/installer && make deps)
+            exit 0
+        name: 'Installer dependencies'
+        triggeredBy:
+            - postDevcontainerStart
+    buildTypescript:
+        command: yarn --network-timeout 100000 && yarn build
+        name: 'TypeScript: install and build'
+        triggeredBy:
+            - postDevcontainerStart
+    setupPreCommit:
+        command: |
+            pre-commit install --install-hooks
+            exit 0
+        name: 'Install pre-commit hooks'
+        triggeredBy:
+            - postDevcontainerStart
+    initGo:
+        command: |
+            ./components/gitpod-protocol/go/scripts/generate-config.sh
+            leeway exec --filter-type go -v -- go mod verify
+        name: 'Go: init'
+        triggeredBy:
+            - postDevcontainerStart
diff --git a/dev/install-dependencies.sh b/dev/install-dependencies.sh
deleted file mode 100755
index dc674943d0da64..00000000000000
--- a/dev/install-dependencies.sh
+++ /dev/null
@@ -1,7 +0,0 @@
-#!/bin/bash
-
-git config --global alias.lg "log --color --graph --pretty=format:'%Cred%h%Creset -%C(yellow)%d%Creset %s %Cgreen(%cr) %C(bold blue)<%an>%Creset' --abbrev-commit"
-leeway run dev/preview:configure-workspace
-leeway run dev:install-dev-utils
-leeway run dev/preview/previewctl:install
-pre-commit install --install-hooks