diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index 4ca239a8..616dce1d 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -3,6 +3,7 @@
     "dockerComposeFile": "./docker-compose.yaml",
     "service": "devcontainer-roboflow-python",
     "workspaceFolder": "/roboflow-python",
+    "initializeCommand": "sh -lc 'mkdir -p .devcontainer/certs; if command -v mkcert >/dev/null 2>&1; then CAROOT=\"$(mkcert -CAROOT)\"; if [ -f \"$CAROOT/rootCA.pem\" ]; then cp \"$CAROOT/rootCA.pem\" .devcontainer/certs/mkcert-rootCA.crt; else echo \"[devcontainer] mkcert CA not found at $CAROOT/rootCA.pem; skipping\"; fi; else echo \"[devcontainer] mkcert not installed; skipping CA copy\"; fi'",
     "postStartCommand": "git config --global --add safe.directory ${containerWorkspaceFolder}",
     "customizations": {
         "vscode": {
diff --git a/.devcontainer/docker-compose.yaml b/.devcontainer/docker-compose.yaml
index 2b384ece..231cf405 100644
--- a/.devcontainer/docker-compose.yaml
+++ b/.devcontainer/docker-compose.yaml
@@ -5,6 +5,8 @@ services:
       context: ..
       dockerfile: Dockerfile.dev
     image: devcontainer-roboflow-python
+    extra_hosts:
+      - "localhost.roboflow.one:host-gateway"
     volumes:
       - ..:/roboflow-python
     command: sleep infinity
diff --git a/.gitignore b/.gitignore
index fdf9d00c..00ea342a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,6 +8,7 @@ __pycache__/
 .idea
 # C extensions
 *.so
+.devcontainer/certs/
 
 # Distribution / packaging
 .Python
diff --git a/Dockerfile.dev b/Dockerfile.dev
index e1d6b9af..1f604c88 100644
--- a/Dockerfile.dev
+++ b/Dockerfile.dev
@@ -1,12 +1,20 @@
 FROM python:3.10
-RUN apt-get update && apt-get install -y make curl libgl1-mesa-glx && rm -rf /var/lib/apt/lists/*
+RUN apt-get update && apt-get install -y make curl libgl1-mesa-glx ca-certificates && rm -rf /var/lib/apt/lists/*
 RUN curl -LsSf https://astral.sh/uv/install.sh | sh
 ENV PATH="/root/.local/bin:${PATH}"
 
+
 WORKDIR /roboflow-python
 COPY .devcontainer/bashrc_ext /root/bashrc_ext
 RUN echo "source /root/bashrc_ext" >> ~/.bashrc
 
+# Trust any custom CAs provided in build context (e.g., mkcert)
+COPY .devcontainer/certs/ /usr/local/share/ca-certificates/
+RUN update-ca-certificates || true
+ENV SSL_CERT_FILE=/etc/ssl/certs/ca-certificates.crt
+ENV REQUESTS_CA_BUNDLE=/etc/ssl/certs/ca-certificates.crt
+
+
 COPY ./requirements.txt ./
 RUN uv pip install --system -r requirements.txt