diff --git a/.devcontainer/squid-https-test/.gitignore b/.devcontainer/squid-https-test/.gitignore
new file mode 100644
index 0000000..4feb3e6
--- /dev/null
+++ b/.devcontainer/squid-https-test/.gitignore
@@ -0,0 +1 @@
+squid-ssl
diff --git a/.devcontainer/squid-https-test/.vscode/tasks.json b/.devcontainer/squid-https-test/.vscode/tasks.json
new file mode 100644
index 0000000..e6b1ed8
--- /dev/null
+++ b/.devcontainer/squid-https-test/.vscode/tasks.json
@@ -0,0 +1,13 @@
+{
+    "version": "2.0.0",
+    "tasks": [
+        {
+            "label": "squid",
+            "type": "shell",
+            "command": "stunnel /etc/stunnel/stunnel.conf & squid -N -d1 -f /etc/squid/squid.conf & sleep 2 && tail -n +1 -F /var/log/squid/access.log",
+            "runOptions": {
+                "runOn": "folderOpen"
+            }
+        }
+    ]
+}
diff --git a/.devcontainer/squid-https-test/Dockerfile b/.devcontainer/squid-https-test/Dockerfile
new file mode 100644
index 0000000..b7b0b10
--- /dev/null
+++ b/.devcontainer/squid-https-test/Dockerfile
@@ -0,0 +1,20 @@
+FROM ubuntu:latest
+
+# squid-openssl is the Squid build with OpenSSL / SSL-Bump (TLS interception) support.
+# stunnel provides the TLS-terminating proxy port in front of Squid.
+RUN apt-get update \
+	&& apt-get install -y \
+		squid-openssl \
+		stunnel4 \
+		openssl \
+		ca-certificates \
+		iputils-ping \
+		dnsutils \
+	&& rm -rf /var/lib/apt/lists/*
+
+COPY squid.conf /etc/squid/squid.conf
+COPY stunnel.conf /etc/stunnel/stunnel.conf
+COPY setup.sh /usr/local/bin/setup.sh
+RUN chmod +x /usr/local/bin/setup.sh
+
+CMD ["sleep", "inf"]
diff --git a/.devcontainer/squid-https-test/README.md b/.devcontainer/squid-https-test/README.md
new file mode 100644
index 0000000..5259a0e
--- /dev/null
+++ b/.devcontainer/squid-https-test/README.md
@@ -0,0 +1,12 @@
+## Squid HTTPS Test
+
+A second TLS-intercepting proxy (in addition to the mitmproxy-based `HTTPS Proxy Test`), using Squid with SSL-Bump behind stunnel.
+
+Squid can only do SSL-Bump on an explicit HTTP `http_port` (it bumps the tunneled TLS of each `CONNECT`), not on an explicit TLS `https_port`. To still expose a real TLS proxy port, stunnel terminates TLS on port `3128` and forwards the decrypted proxy traffic to Squid's localhost-only `http_port`, where SSL-Bump intercepts the connections. A single CA signs both the proxy's `localhost` certificate and the per-host certificates Squid generates, so you only install one certificate on the host.
+
+- `Dev Containers: Reopen in Container` > `Squid HTTPS Test`.
+- The dev container should show two log terminals: one for Squid and one for stunnel (the TLS proxy port).
+- First time: Install the CA certificate from `.devcontainer/squid-https-test/squid-ssl/ca.crt` in the OS trust store and restart VS Code. The certificate is generated on the first container start, so it only appears after the container is up.
+- Add the user setting `"http.proxy": "https://localhost:3133"`.
+- Install GitHub Copilot Chat and use `Developer: GitHub Copilot Chat Diagnostics` to test connections with a HTTPS proxy. Use a second window to test connections from a local extension host.
+- Verify in the log terminals of the dev container that the proxy is being used.
diff --git a/.devcontainer/squid-https-test/devcontainer-lock.json b/.devcontainer/squid-https-test/devcontainer-lock.json
new file mode 100644
index 0000000..219acb6
--- /dev/null
+++ b/.devcontainer/squid-https-test/devcontainer-lock.json
@@ -0,0 +1,3 @@
+{
+  "features": {}
+}
diff --git a/.devcontainer/squid-https-test/devcontainer.json b/.devcontainer/squid-https-test/devcontainer.json
new file mode 100644
index 0000000..2d1b68d
--- /dev/null
+++ b/.devcontainer/squid-https-test/devcontainer.json
@@ -0,0 +1,6 @@
+{
+	"name": "Squid HTTPS Test",
+	"dockerComposeFile": "docker-compose.yml",
+	"service": "devcontainer",
+	"workspaceFolder": "/workspaces/${localWorkspaceFolderBasename}/.devcontainer/squid-https-test"
+}
diff --git a/.devcontainer/squid-https-test/docker-compose.yml b/.devcontainer/squid-https-test/docker-compose.yml
new file mode 100644
index 0000000..c0dc43a
--- /dev/null
+++ b/.devcontainer/squid-https-test/docker-compose.yml
@@ -0,0 +1,13 @@
+version: '3.4'
+
+services:
+    devcontainer:
+        build:
+            context: .
+            dockerfile: Dockerfile
+        volumes:
+          - ../../..:/workspaces
+          - ./squid-ssl:/etc/squid/ssl
+        ports:
+            - "127.0.0.1:3133:3128"
+        command: /bin/sh -c "/usr/local/bin/setup.sh && sleep inf"
diff --git a/.devcontainer/squid-https-test/setup.sh b/.devcontainer/squid-https-test/setup.sh
new file mode 100644
index 0000000..ed7e563
--- /dev/null
+++ b/.devcontainer/squid-https-test/setup.sh
@@ -0,0 +1,54 @@
+#!/bin/bash
+# Generates the CA used as the signing CA for the certificates Squid generates
+# on the fly when bumping (intercepting) TLS connections, plus the localhost
+# server certificate stunnel presents on the TLS proxy port. Both are signed by
+# the same CA, so installing ca.crt in the host trust store covers everything.
+# Idempotent: safe to run on every start.
+set -e
+
+SSL_DIR=/etc/squid/ssl
+SSL_DB=/var/lib/squid/ssl_db
+
+mkdir -p "$SSL_DIR"
+
+if [ ! -f "$SSL_DIR/ca.crt" ] || [ ! -f "$SSL_DIR/ca.key" ]; then
+	echo "Generating CA certificate ..."
+	openssl req -x509 -newkey rsa:2048 -sha256 -days 3650 -nodes \
+		-keyout "$SSL_DIR/ca.key" \
+		-out "$SSL_DIR/ca.crt" \
+		-subj "/CN=Squid HTTPS Test CA" \
+		-addext "basicConstraints=critical,CA:TRUE" \
+		-addext "keyUsage=critical,keyCertSign,cRLSign"
+fi
+
+# The localhost server certificate stunnel presents on the TLS proxy port.
+if [ ! -f "$SSL_DIR/proxy.crt" ] || [ ! -f "$SSL_DIR/proxy.key" ]; then
+	echo "Generating proxy server certificate ..."
+	openssl req -new -newkey rsa:2048 -nodes \
+		-keyout "$SSL_DIR/proxy.key" \
+		-out "$SSL_DIR/proxy.csr" \
+		-subj "/CN=localhost"
+	# macOS (SecTrustEvaluateWithError) enforces Apple's TLS server cert policy:
+	# leaf validity must be <= 398 days and the serverAuth EKU must be present,
+	# otherwise the cert is rejected as "not standards compliant" (errSecCertificateNotStandardsCompliant / -67901).
+	openssl x509 -req -in "$SSL_DIR/proxy.csr" \
+		-CA "$SSL_DIR/ca.crt" -CAkey "$SSL_DIR/ca.key" -CAcreateserial \
+		-out "$SSL_DIR/proxy.crt" -days 397 -sha256 \
+		-extfile <(printf "subjectAltName=DNS:localhost,IP:127.0.0.1\nbasicConstraints=CA:FALSE\nkeyUsage=digitalSignature,keyEncipherment\nextendedKeyUsage=serverAuth")
+	rm -f "$SSL_DIR/proxy.csr"
+fi
+
+# Squid drops privileges to the 'proxy' user, which must be able to read the key.
+chmod 644 "$SSL_DIR/ca.crt" "$SSL_DIR/proxy.crt"
+chmod 640 "$SSL_DIR/ca.key" "$SSL_DIR/proxy.key"
+chgrp proxy "$SSL_DIR/ca.key" 2>/dev/null || true
+
+# Initialize the database used to cache the per-host certificates Squid generates.
+if [ ! -d "$SSL_DB" ]; then
+	echo "Initializing SSL certificate database ..."
+	mkdir -p "$(dirname "$SSL_DB")"
+	/usr/lib/squid/security_file_certgen -c -s "$SSL_DB" -M 20MB
+fi
+chown -R proxy:proxy "$SSL_DB" 2>/dev/null || true
+
+echo "CA certificate to install on the host: .devcontainer/squid-https-test/squid-ssl/ca.crt"
diff --git a/.devcontainer/squid-https-test/squid.conf b/.devcontainer/squid-https-test/squid.conf
new file mode 100644
index 0000000..9ce95cf
--- /dev/null
+++ b/.devcontainer/squid-https-test/squid.conf
@@ -0,0 +1,28 @@
+# Minimal Squid configuration for a TLS-intercepting proxy.
+#
+# The TLS-terminating proxy port is provided by stunnel (see stunnel.conf), which
+# forwards the decrypted proxy traffic to this plaintext, localhost-only port.
+# Squid is a normal HTTP forward proxy here; SSL-Bump intercepts (bumps) the
+# tunneled TLS connections established via CONNECT. The CA (ca.crt / ca.key) is
+# the signing CA for the per-host certificates Squid generates on the fly.
+# (Squid only allows ssl-bump on http_port for explicit forward proxies, not on
+# an explicit https_port.)
+
+http_port 127.0.0.1:3130 ssl-bump cert=/etc/squid/ssl/ca.crt key=/etc/squid/ssl/ca.key \
+    generate-host-certificates=on dynamic_cert_mem_cache_size=20MB
+
+sslcrtd_program /usr/lib/squid/security_file_certgen -s /var/lib/squid/ssl_db -M 20MB
+sslcrtd_children 5
+
+acl step1 at_step SslBump1
+ssl_bump peek step1
+ssl_bump bump all
+
+http_access allow all
+
+# Squid runs as the 'proxy' user and cannot write to /dev/stdout, so log to
+# files under /var/log/squid; the `squid` task tails them into the terminal.
+logfile_rotate 0
+access_log stdio:/var/log/squid/access.log squid
+
+coredump_dir /var/spool/squid
diff --git a/.devcontainer/squid-https-test/stunnel.conf b/.devcontainer/squid-https-test/stunnel.conf
new file mode 100644
index 0000000..e7569de
--- /dev/null
+++ b/.devcontainer/squid-https-test/stunnel.conf
@@ -0,0 +1,15 @@
+# stunnel provides the TLS-terminating HTTPS proxy port. It accepts TLS on 3128
+# (presenting the localhost server certificate) and forwards the decrypted proxy
+# traffic to Squid's plaintext, localhost-only port, where SSL-Bump intercepts
+# the tunneled TLS connections.
+
+foreground = yes
+pid =
+debug = 4
+output = /dev/stdout
+
+[https-proxy]
+accept = 0.0.0.0:3128
+connect = 127.0.0.1:3130
+cert = /etc/squid/ssl/proxy.crt
+key = /etc/squid/ssl/proxy.key