diff --git a/.devcontainer/Dockerfile b/.devcontainer/Dockerfile
index 1e223d8ef..2e898deec 100644
--- a/.devcontainer/Dockerfile
+++ b/.devcontainer/Dockerfile
@@ -2,4 +2,6 @@ FROM ghcr.io/goauthentik/server:latest
 
 USER root
 
-RUN pip install --no-cache-dir -r /requirements-dev.txt
+HEALTHCHECK --interval=10s CMD exit 0
+
+RUN pip install --no-cache-dir -r /app-root/requirements-dev.txt
diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index 44155bf85..edf5b5ace 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -2,7 +2,7 @@
     "name": "authentik",
     "dockerComposeFile": "docker-compose.yml",
     "service": "app",
-    "workspaceFolder": "/authentik",
+    "workspaceFolder": "/app-root",
     "features": {
         "ghcr.io/devcontainers/features/docker-outside-of-docker:1": {},
         "ghcr.io/devcontainers/features/go:1": {},
diff --git a/.devcontainer/docker-compose.yml b/.devcontainer/docker-compose.yml
index 378cfb04c..d0c461ce1 100644
--- a/.devcontainer/docker-compose.yml
+++ b/.devcontainer/docker-compose.yml
@@ -6,8 +6,13 @@ services:
       context: ..
       dockerfile: .devcontainer/Dockerfile
     volumes:
-      - ../:/authentik:cached
+      - ../:/app-root:cached
     command: debug
+    environment:
+      AUTHENTIK_POSTGRESQL__USER: postgres
+      AUTHENTIK_POSTGRESQL__PASSWORD: postgres
+      AUTHENTIK_BOOTSTRAP_PASSWORD: akadmin
+      AUTHENTIK_BOOTSTRAP_TOKEN: akadmin
   db:
     image: docker.io/library/postgres:15
     restart: unless-stopped
@@ -16,7 +21,7 @@ services:
     network_mode: service:app
     environment:
       POSTGRES_USER: postgres
-      POSTGRES_DB: postgres
+      POSTGRES_DB: authentik
       POSTGRES_PASSWORD: postgres
   redis:
     image: docker.io/redis/redis-stack-server
diff --git a/.vscode/tasks.json b/.vscode/tasks.json
index cd705afff..61762272e 100644
--- a/.vscode/tasks.json
+++ b/.vscode/tasks.json
@@ -3,26 +3,23 @@
     "tasks": [
         {
             "label": "authentik[core]: format & test",
-            "command": "poetry",
-            "args": [
-                "run",
-                "make"
-            ],
+            "command": "make",
             "group": "build",
         },
         {
             "label": "authentik[core]: run",
-            "command": "poetry",
+            "command": "ak",
             "args": [
-                "run",
-                "make",
-                "run",
+                "server",
             ],
             "group": "build",
             "presentation": {
                 "panel": "dedicated",
                 "group": "running"
             },
+            "runOptions": {
+                "runOn": "folderOpen"
+            }
         },
         {
             "label": "authentik[web]: format",
@@ -39,6 +36,9 @@
                 "panel": "dedicated",
                 "group": "running"
             },
+            "runOptions": {
+                "runOn": "folderOpen"
+            }
         },
         {
             "label": "authentik: install",
diff --git a/Dockerfile b/Dockerfile
index 7c9dab3e3..d899f21dd 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -84,7 +84,7 @@ RUN apt-get update && \
     apt-get install -y --no-install-recommends libxmlsec1-openssl libmaxminddb0 && \
     # Required for bootstrap & healtcheck
     apt-get install -y --no-install-recommends runit && \
-    pip install --no-cache-dir -r /requirements.txt && \
+    pip install --no-cache-dir -r /app-root/requirements.txt && \
     apt-get remove --purge -y build-essential pkg-config libxmlsec1-dev && \
     apt-get autoremove --purge -y && \
     apt-get clean && \
@@ -111,7 +111,7 @@ USER 1000
 
 ENV TMPDIR /dev/shm/
 ENV PYTHONUNBUFFERED 1
-ENV PATH "/usr/local/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/lifecycle"
+ENV PATH "/usr/local/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/app-root/lifecycle"
 
 HEALTHCHECK --interval=30s --timeout=30s --start-period=60s --retries=3 CMD [ "ak", "healthcheck" ]