Tunnel Doctor

Tunnel Doctor

Diagnose and fix conflicts when Tailscale coexists with proxy/VPN tools on macOS, with specific guidance for SSH access to WSL instances.

Methodology base: the general diagnostic discipline this skill builds on — evidence over assumption, falsification over confirmation, layered isolation, counter-review — lives in the debugging-network-issues skill. This skill is the macOS Tailscale⨯proxy domain layer on top of it; reach for the base skill when the symptom is not a known Tailscale/proxy conflict.

Ownership boundary: this skill owns concrete local network-path operations: Tailscale, route/DNS/proxy interception, VM/WSL propagation, TUN forwarding planes, and proxy node/exit/chain capacity. Use debugging-network-issues as the general method when the boundary is still unknown or the symptom belongs to SSE/CDN/application protocol behavior. This keeps one concrete operator instead of forcing the user to choose between two overlapping proxy doctors.

Target and task scope

Before remote probes or changes, establish whether the target is a designated test machine, an explicitly requested colleague's working computer, or unknown. Use the owner's existing machine-purpose ledger and current task; do not log into a colleague's machine to classify it. Saved SSH access and previous successful tests do not grant ongoing use. Use designated test machines for routine testing; their unavailability does not authorize another person's computer.

Keep an explicitly requested one-off test on a colleague's computer within its stated result and necessary verification. Stop there on completion, cancellation, or a need for an unapproved environment change. Move later performance, migration, and regression tests to designated test machines. A test failure does not authorize disabling that person's proxy/VPN, quitting apps, changing routes, or installing a background task. Proceed with disruptive repair there only when the user has explicitly requested that repair and its interruption. Existing authorization for owner test-machine maintenance remains valid; do not ask again for its routine steps.

Apply this boundary even when invoked directly, through another Skill, after compaction, or through a peer handoff. After access is stopped, use existing records rather than another SSH probe to verify that it stopped.

Disruptive network changes

Before any authorized VPN disconnect, app termination, route cutover, or service restart, read network_change_recovery.md. Validate prerequisites before interruption, arm bounded recovery before the first disruptive action, and verify both the repaired path and the user's original network use. A successful stop command, a detached process, or a restart placed at the end of a script is not recovery evidence.

Conflict Layers

Proxy/VPN tools on macOS create conflicts at several independent layers. Layers 1-3 affect Tailscale connectivity; Layer 4 affects SSH git operations; Layer 5 affects VM/container runtimes. TUN-state failure modes beyond this table — SSH/git connection drops, resolver stall, DIRECT split-brain — are covered in Steps 2H–2J:

Diagnostic Workflow

Step 1: Identify the Symptom

Determine which scenario applies:

• Browser returns HTTP 503, but curl and SSH both work → System proxy bypass conflict (Step 2C)
• local.<domain> fails in browser/default curl, but direct/no-proxy request works → Local vanity domain proxy interception (Step 2C-1)
• Tailscale ping works, SSH works, but curl/HTTP times out → HTTP proxy env var conflict (Step 2A)
• Tailscale ping works, SSH/TCP times out → Route conflict (Step 2B)
• Remote dev server auth redirects to localhost → browser can't follow → SSH tunnel needed (Step 2D)
• make status / scripts curl to localhost fail with proxy → localhost proxy interception (Step 2E)
• git push/pull fails with FATAL: failed to begin relaying via HTTP → SSH double tunnel (Step 2F)
• docker build RUN apk/apt fails with Connection refused instantly → OrbStack transparent proxy + TUN conflict (Step 2G-1, fix: --network host)
• docker pull fails with TLS handshake timeout → VM proxy misconfiguration (Step 2G-2, fix: docker.json with host.internal)
• Container healthcheck (unhealthy) but app runs fine → Lowercase proxy env var leak (Step 2G-4, fix: clear http_proxy+HTTP_PROXY)
• docker build can't fetch base images → VM/container proxy propagation (Step 2G)
• docker pull works but docker build still dies fetching base-image tokens (TLS/i-o timeout) on a WSL2 + Docker Desktop host, or every runbook proxy port on a Windows+v2rayN host silently died after a v2rayN upgrade → buildkit direct-dials past the DD proxy override / v2rayN ≥7.17 LAN-port split (references/windows_host_tun_wsl_cascade.md §2026-08-23)
• git clone fails with Connection closed by 198.18.x.x → two different mechanisms produce this; Step 2H separates them
• Every domestic/DIRECT-rule site fails at once (TLS unexpected EOF mid-handshake, proxy-port CONNECT returns 503, Node CLIs report UNKNOWN_CERTIFICATE_VERIFICATION_ERROR) while proxied overseas sites keep working → TUN DIRECT split-brain (Step 2J)
• SSH connects but operation not permitted → Tailscale SSH config issue (Step 4)
• SSH connects but be-child ssh exits code 1 → WSL snap sandbox issue (Step 5)
• TCP port 22 reachable (nc -z succeeds) but SSH fails with kex_exchange_identification: Connection closed → Tailscale SSH proxy intercept on WSL (Step 5A)
• Same kex_exchange_identification / Connection closed by UNKNOWN port 65535, but there is no Tailscale — you are behind a TUN and the host is a public cloud VM whose HTTPS still works → could be your TUN or the destination's firewall allowlist; they are indistinguishable from the client. Step 2K settles it out-of-band
• tailscale ssh returns "not available on App Store builds" → Wrong Tailscale distribution on macOS (Step 5B)
• Any tool using system DNS (ssh, curl, git) hangs ~60s before resolving, but nslookup returns instantly → Stalled resolver in getaddrinfo chain (Step 2I)
• Windows+WSL host: everything offline at once (domestic AND overseas), WSL dead too, "even Tailscale won't come online" — and/or the user tried several recovery actions (switched NICs, toggled TUN) and can't tell which one fixed it → Windows host TUN cascade + event-log forensics (Step 5C)
• Tailscale, DNS, route ownership, and proxy reachability all pass, but large transfers remain slow and switching the active proxy node changes throughput → proxy node / exit / chain capacity workflow in references/proxy_node_chain_throughput.md

Key distinctions:

• SSH does NOT use http_proxy/NO_PROXY env vars. If SSH works but HTTP doesn't → Layer 2.
• curl uses http_proxy env var, NOT the system proxy. Browser uses system proxy (set by VPN). If curl works but browser doesn't → Layer 3.
• If tailscale ping works but regular ping doesn't → Layer 1 (route table corrupted).
• If ssh -T git@github.com works but git push fails intermittently → Layer 4 (double tunnel).
• If host curl https://... works but docker pull times out → Layer 5 (VM proxy propagation).
• If docker pull works but docker build RUN apk add fails instantly with Connection refused → OrbStack transparent proxy broken by TUN (Step 2G-1).
• If container healthcheck shows (unhealthy) but app works → lowercase http_proxy leaked into container (Step 2G-4).
• If DNS resolves to 198.18.x.x virtual IPs → a TUN is active, which is not by itself a diagnosis: under TUN every hostname resolves this way, on success as well as failure. Go to Step 2H to find out which mechanism you have.
• If connections to fake-IP-resolved domains die but the same host works via curl --resolve <host>:443:<real-ip> (real IP from dig @<public-resolver>) → the TUN tool's DIRECT forwarding state is broken, not your network and not the destination (Step 2J).
• If nc -z succeeds on port 22 but SSH gets no banner (kex_exchange_identification) → Tailscale SSH proxy intercept (Step 5A). Confirm with tcpdump -i any port 22 on the remote — 0 packets means Tailscale intercepts above the kernel.
• If nc -z also succeeds on a port the destination does not serve (probe 65001) → under a TUN the local stack answers for the destination, so no nc -z result on that host means anything. Never read a port probe you have not calibrated this way. This supersedes the plain nc -z reading in the bullet above whenever a TUN — not just Tailscale — is in the path (Step 2K).
• If the destination's own journalctl -u ssh shows zero entries for your attempts → something before sshd is eating them, but not necessarily the network: a host-local packet filter drops them just as silently. tcpdump on the host separates "never arrived" from "arrived and was dropped locally"; only the first implicates your TUN. Reach the machine through the cloud provider's guest-agent channel to ask, since that path does not use the port you cannot reach. Check the journal, not auth.log: on Ubuntu 24.04 sshd writes nothing to auth.log, so an empty file there is not evidence (Step 2K).
• A cloud host enforces an inbound port twice — provider security group and host firewall (ufw/firewalld/nftables). Adding your IP to one leaves the other blocking, with no signal that you only did half the job (Step 2K).
• If tailscale ssh fails with "not available on App Store builds" → install Standalone Tailscale (Step 5B).
• If nslookup <host> is fast (<0.1s) but dscacheutil -q host -a name <host> takes 60s+ → a supplemental resolver in scutil --dns is dead (Step 2I).
• If ping <resolver-ip> succeeds but dig @<resolver-ip> times out → daemon dead, utun interface zombied. ICMP is answered by the interface; the actual port-53 service is gone (Step 2I).
• If ssh -vvv hangs immediately after debug2: resolving "<host>" port <port> and never reaches debug1: connect to address → DNS resolution stage, not network connect stage. This is Step 2I, not Step 2B/2H.

Diagnosis Discipline (Read Before Committing to a Hypothesis)

When symptoms point at a component (proxy, VPN, route table, DNS), don't commit to a hypothesis from circumstantial evidence — verify with that component's own health endpoint first. Each component has a one-line health check faster and more reliable than ruling out neighbors:

Why this matters: A symptom that matches the description of Step 2X does not, by itself, prove component X is the problem. Multiple layers can produce overlapping symptoms (a 60-second hang during git push could be proxy node death, fakeip route corruption, or DNS resolver stall — all plausible from the user-visible symptom alone). Reaching for the most specific verification first avoids committing to a wrong layer and chasing it down a dead end.

If the failing operation involves DNS at all, run the per-nameserver bisection from Step 2I before suspecting proxy or routing. It rules in/out the largest single class of macOS-on-China-network failures in under 15 seconds.

TUN Measurement Contamination (what your probes lie about while a TUN proxy is up)

When a proxy tool runs in TUN / global mode (Shadowrocket, Clash, Surge), it intercepts traffic at the routing layer and fabricates parts of the network stack locally. Several everyday diagnostic commands then return fabricated or misrouted numbers — trusting them sends the whole investigation the wrong way. Know what each probe actually measures under TUN:

What you can trust under TUN:

• time_appconnect / time_starttransfer from curl (application-layer handshake / TTFB) — these complete only after the tunneled connection actually establishes, so they reflect the real end-to-end path.
• An in-region / domestic IP-geo source for "what is my real local ISP" — an in-region domain hits the proxy's DIRECT rule and exits your real last mile (the foreign source gets tunneled and lies; see table).
• The proxy/TUN config decoded from disk + the tool's own GUI — the authoritative source of which node/route is actually active. Cross-check a file parse against the GUI; do not infer the active node from a network probe.

Counter-move: before citing any latency / reachability number while a TUN is up, ask "would this number be physically possible if the packet really traversed to the destination?" A 0.00s connect or a 0.2ms ping to another continent is the tell that you measured the TUN, not the network. Switch to time_appconnect, or temporarily disable the TUN to get a clean baseline (raw probes become meaningful again once it is off).

Fast Path: Run Automated Checks

For common macOS conflicts (env proxy, system proxy exceptions, direct/proxy path split, local TLS trust), run:

python3 scripts/quick_diagnose.py --host local.example.com --url https://local.example.com/health

Optional route ownership check for a Tailscale destination:

python3 scripts/quick_diagnose.py --host <target-host> --url http://<target-host>:<port>/health --tailscale-ip <100.x.x.x>

Interpretation:

• direct=PASS + forced_proxy=FAIL = host must bypass proxy (skip-proxy + NO_PROXY).
• strict_tls=FAIL + direct=PASS = path is reachable; trust issue only (install/trust local CA).
• host in scutil exceptions: no = browser/system clients still likely proxied.

Step 2A: Fix HTTP Proxy Environment Variables

Check if proxy env vars are intercepting Tailscale HTTP traffic:

env | grep -i proxy

Broken output — proxy is set but NO_PROXY doesn't exclude Tailscale:

http_proxy=http://127.0.0.1:1082
https_proxy=http://127.0.0.1:1082
NO_PROXY=localhost,127.0.0.1          ← Missing Tailscale!

Fix — add Tailscale MagicDNS domain + CIDR to NO_PROXY:

export NO_PROXY=localhost,127.0.0.1,.ts.net,100.64.0.0/10,192.168.*,10.*,172.16.*

Two layers complement each other: .ts.net handles domain-based access, 100.64.0.0/10 handles direct IP access.

NO_PROXY syntax pitfalls — see references/proxy_conflict_reference.md for the compatibility matrix.

Go net/http CIDR caveat: Go's standard net/http does NOT support CIDR notation in NO_PROXY. Setting NO_PROXY=100.64.0.0/10 works for curl and Python, but Go programs (including Tailscale-adjacent tooling) will still send traffic through the proxy. The fix is to use MagicDNS hostnames (e.g., my-wsl-box) instead of raw IPs, or add explicit hostnames to NO_PROXY:

# WRONG for Go programs — CIDR is silently ignored
NO_PROXY=100.64.0.0/10 go-program http://100.101.102.103:8002/health  # → goes through proxy

# CORRECT — use hostname (matched as suffix) or explicit IP
export NO_PROXY=localhost,127.0.0.1,.ts.net,my-wsl-box,100.101.102.103,192.168.*,10.*,172.16.*

This is especially relevant when accessing Tailscale services from Go-based tools (e.g., custom CLIs, Go test suites hitting remote APIs).

Verify the fix:

# Both must return HTTP 200:
NO_PROXY="...(new value)..." curl -s --connect-timeout 5 http://<host>.ts.net:<port>/health -w "HTTP %{http_code}\n"
NO_PROXY="...(new value)..." curl -s --connect-timeout 5 http://<tailscale-ip>:<port>/health -w "HTTP %{http_code}\n"

Then persist in shell config (~/.zshrc or ~/.bashrc).

Step 2B: Detect Route Conflicts

Check if a proxy tool hijacked the Tailscale CGNAT range:

route -n get <tailscale-ip>

Healthy output — traffic goes through Tailscale interface:

destination: 100.64.0.0
interface: utun7    # Tailscale interface (utunN varies)

Broken output — proxy hijacked the route:

destination: 100.64.0.0
gateway: 192.168.x.1    # Default gateway
interface: en0           # Physical interface, NOT Tailscale

Important: Not all utun interfaces are Tailscale's. Verify which utun belongs to Tailscale before concluding the route is correct:

# Find Tailscale's utun interface (has a 100.x.x.x IP)
ifconfig | grep -A2 'inet 100\.'

Quick indicators by MTU:

• MTU 1280 → typically Tailscale
• MTU 4064 → typically Shadowrocket TUN

If route -n get shows traffic going to a utun with MTU 4064, it is hitting Shadowrocket's TUN, not Tailscale — this is still a route conflict even though the interface name starts with utun.

Confirm with full route table:

netstat -rn | grep 100.64

Two competing routes indicate a conflict:

100.64/10  192.168.x.1   UGSc  en0       ← Proxy added this (wins)
100.64/10  link#N        UCSI  utun7     ← Tailscale route (loses)

Root cause: On macOS, UGSc (Static Gateway) takes priority over UCSI (Cloned Static Interface) for the same prefix length.

Step 2C: Fix System Proxy Bypass (Browser 503)

Symptom: Browser shows HTTP 503 for http://<tailscale-ip>:<port>, but both curl --noproxy '*' and curl (with proxy env var) return 200. SSH also works.

Root cause: The browser uses the system proxy configured by the VPN profile (Shadowrocket/Clash/Surge). The proxy matches IP-CIDR,100.64.0.0/10,DIRECT and tries to connect directly — but "directly" means via the Wi-Fi interface (en0), NOT through Tailscale's utun interface. The proxy process itself doesn't have a route to Tailscale IPs, so the connection fails with 503.

Diagnosis:

# curl with proxy env var works (curl connects to proxy port, but traffic flows differently)
curl -s -o /dev/null -w "%{http_code}" http://<tailscale-ip>:<port>/
# → 200

# Browser gets 503 because it goes through the VPN system proxy, not http_proxy env var

Fix — add Tailscale CGNAT range to skip-proxy in the proxy tool config:

For Shadowrocket, in [General]:

skip-proxy = 192.168.0.0/16, 10.0.0.0/8, 172.16.0.0/12, 100.64.0.0/10, localhost, *.local, captive.apple.com

skip-proxy tells the system "bypass the proxy entirely for these addresses." The browser then connects directly through the OS network stack, where Tailscale's routing table correctly handles the traffic.

Why skip-proxy works but tun-excluded-routes doesn't:

• skip-proxy: Bypasses the HTTP proxy layer only. Traffic still flows through the TUN interface and Tailscale utun handles it. Safe.
• tun-excluded-routes: Removes the CIDR from the TUN routing entirely. This creates a competing en0 route that overrides Tailscale. Breaks everything.

Step 2C-1: Fix Local Vanity Domain Interception (local.<domain>)

Symptom: https://local.<domain> fails in browser or default curl, but succeeds with direct/no-proxy command:

env -u http_proxy -u https_proxy curl -k -I https://local.<domain>/health
# -> 200
curl -I https://local.<domain>/health
# -> proxy CONNECT then TLS reset/failure

Root cause: The domain is routed through system/shell proxy instead of local direct path.

Fix:

1. Add domain to proxy app bypass list (skip-proxy for Shadowrocket).
2. Add domain to shell bypass list (NO_PROXY/no_proxy).
3. If local TLS uses internal CA, trust the local root certificate.

# ~/.zshrc
export NO_PROXY=localhost,127.0.0.1,.ts.net,100.64.0.0/10,192.168.*,10.*,172.16.*,local.<domain>,www.local.<domain>
export no_proxy="$NO_PROXY"

Verification:

python3 scripts/quick_diagnose.py --host local.<domain> --url https://local.<domain>/health

Expected:

• host in NO_PROXY: yes
• host in scutil exceptions: yes
• ambient=PASS and direct=PASS

Step 2D: Fix Auth Redirect for Remote Dev (SSH Tunnel)

Symptom: Dev server runs on a remote machine (e.g., Mac Mini via Tailscale). You access http://<tailscale-ip>:3010 in the browser. Login/signup works, but after auth, the app redirects to http://localhost:3010/ which fails — localhost on your machine isn't running the dev server.

Root cause: The app's APP_URL (or equivalent) is set to http://localhost:3010. Auth libraries (Better-Auth, NextAuth, etc.) use this URL for callback redirects. Changing APP_URL to the Tailscale IP introduces Shadowrocket proxy conflicts and breaks local development on the remote machine.

Fix — SSH local port forwarding. This avoids all three conflict layers entirely:

# Forward local port 3010 to remote machine's localhost:3010
ssh -NL 3010:localhost:3010 <tailscale-ip>

# Or with autossh for auto-reconnect (recommended for long sessions)
autossh -M 0 -f -N -L 3010:localhost:3010 \
    -o "ServerAliveInterval=30" \
    -o "ServerAliveCountMax=3" \
    -o "ExitOnForwardFailure=yes" \
    <tailscale-ip>

Now access http://localhost:3010 in the browser. Auth redirects to localhost:3010 → tunnel → remote dev server → works correctly.

Why this is the best approach:

• No .env changes needed — APP_URL=http://localhost:3010 works everywhere
• No Shadowrocket conflicts — localhost is always in skip-proxy
• No code changes — same behavior as local development
• Industry standard — VS Code Remote SSH, GitHub Codespaces use the same pattern

Install autossh: brew install autossh (macOS) or apt install autossh (Linux)

Kill background tunnel: pkill -f 'autossh.*<tailscale-ip>'

Step 2E: Fix localhost Proxy Interception in Scripts

Symptom: Makefile targets or scripts that curl localhost (health checks, warmup routes) fail or timeout when http_proxy is set globally in the shell.

Root cause: http_proxy=http://127.0.0.1:1082 is set in ~/.zshrc but no_proxy doesn't include localhost. All curl commands send localhost requests through the proxy.

Fix — add --noproxy localhost to all localhost curl commands in scripts:

# WRONG — fails when http_proxy is set
@curl -sf http://localhost:9000/minio/health/live && echo "OK"

# CORRECT — always bypasses proxy for localhost
@curl --noproxy localhost -sf http://localhost:9000/minio/health/live && echo "OK"

Alternatively, set no_proxy globally in ~/.zshrc:

export no_proxy=localhost,127.0.0.1

Step 2F: Fix SSH ProxyCommand Double Tunnel (git push/pull failures)

Symptom: ssh -T git@github.com succeeds consistently, but git push or git pull fails intermittently with:

FATAL: failed to begin relaying via HTTP.
Connection closed by UNKNOWN port 65535

Small operations (auth, fetch metadata) work; large data transfers fail.

Root cause: When Shadowrocket TUN is active, it already routes all TCP traffic through its VPN tunnel. If SSH config also uses ProxyCommand connect -H, data flows through two proxy layers — the landing proxy drops large/long-lived HTTP CONNECT connections.

Diagnosis:

# 1. Confirm Shadowrocket TUN is active
ifconfig | grep '^utun'

# 2. Check SSH config for ProxyCommand
grep -A5 'Host github.com' ~/.ssh/config

# 3. Confirm: removing ProxyCommand fixes push
GIT_SSH_COMMAND="ssh -o ProxyCommand=none" git push origin main

Fix — remove ProxyCommand and switch to ssh.github.com:443. See references/proxy_conflict_reference.md § SSH ProxyCommand and Git Operations for the full SSH config, why port 443 helps, and fallback options when VPN is off.

Step 2G: Fix VM/Container Runtime Proxy Propagation (Docker pull/build failures)

Symptom: docker pull or docker build fails with net/http: TLS handshake timeout, Connection refused from Alpine/Debian repos, or Internal Server Error from auth.docker.io, while host curl to the same URLs works fine.

Applies to: OrbStack, Docker Desktop, or any VM-based Docker runtime on macOS with Shadowrocket/Clash TUN active.

Root cause: VM-based Docker runtimes (OrbStack, Docker Desktop) run the Docker daemon inside a lightweight VM. The VM's outbound traffic takes a different network path than host processes:

Host process (curl):   Process → TUN (Shadowrocket) → landing proxy → internet ✅
VM process (Docker):   Docker daemon → VM bridge → host network → TUN → ??? ❌

The TUN handles host-originated traffic correctly but may drop or delay VM-bridged traffic (different TCP stack, MTU, keepalive behavior).

Critical distinction: docker pull vs docker build use different proxy paths:

Fixing docker.json alone will NOT fix docker build — the RUN commands inside the build container don't inherit daemon proxy settings.

Diagnosis — identify which sub-problem:

# 1. Can the Docker daemon pull images?
docker pull --quiet alpine:latest 2>&1

# 2. Can a RUN command inside a build reach the internet?
docker build --no-cache - <<'EOF' 2>&1
FROM alpine:latest
RUN apk update && echo "APK OK"
EOF

# 3. Can a running container reach the internet?
docker run --rm alpine:latest sh -c "apk update 2>&1 | head -3"

Four sub-problems and their fixes:

2G-1: docker build fails but host works (most common with OrbStack + Shadowrocket)

Symptom: RUN apk add or RUN apt-get install inside docker build fails with Connection refused instantly (< 0.2s), even though host curl to the same URL works.

Root cause: OrbStack's network_proxy: auto creates a transparent proxy inside the VM that intercepts all HTTPS traffic. When Shadowrocket TUN is also active, the transparent proxy's upstream connection breaks — it redirects HTTPS to 127.0.0.1 inside the VM, which has nothing listening.

Diagnosis:

# Verify: inside the container, HTTPS goes to 127.0.0.1 (broken transparent proxy)
docker run --rm alpine:latest sh -c "wget -q --timeout=5 -O /dev/null https://dl-cdn.alpinelinux.org/ 2>&1"
# → "wget: can't connect to remote host (127.0.0.1): Connection refused"
#                                        ^^^^^^^^^^^^ This is the smoking gun

# Verify: --network host bypasses the VM bridge and works
docker run --rm --network host alpine:latest sh -c "apk update 2>&1 | head -3"
# → "v3.23.x ... OK: 27431 distinct packages available"  ← Works!

Fix — use --network host for docker build:

docker build --network host -f Dockerfile -t myimage .

This bypasses OrbStack's VM network bridge entirely. The build container uses the host's network stack directly, where Shadowrocket TUN correctly handles traffic.

Trade-off: --network host disables build-time network isolation. For CI/CD, prefer fixing the proxy config (2G-2). For local development, --network host is the pragmatic fix.

Permanent fix — if all your builds need this, add to ~/.docker/daemon.json or use a shell alias:

# Shell alias (add to ~/.zshrc)
alias docker-build='docker build --network host'

2G-2: OrbStack auto-detects and caches proxy config

OrbStack's network_proxy: auto reads http_proxy from the shell environment and configures the Docker daemon. The config is stored in ~/.orbstack/config/docker.json.

Key behaviors:

• network_proxy: auto — OrbStack reads host env, creates transparent proxy in VM
• network_proxy: none — Disables transparent proxy, but VM bridge traffic still routes through TUN (may timeout)
• docker.json — Controls docker pull proxy, NOT docker build RUN commands

Diagnosis:

# Check all three layers
echo "=== OrbStack config ==="
orbctl config get network_proxy

echo "=== docker.json (daemon proxy) ==="
cat ~/.orbstack/config/docker.json

echo "=== Docker info (effective proxy) ==="
docker info | grep -iE "proxy|No Proxy"

Fix — configure docker.json with host.internal (OrbStack resolves this to the host IP):

python3 -c "
import json, os
config = {
    'proxies': {
        'http-proxy': 'http://host.internal:1082',
        'https-proxy': 'http://host.internal:1082',
        'no-proxy': 'localhost,127.0.0.1,::1,192.168.128.0/24,100.64.0.0/10,host.internal,*.local'
    }
}
path = os.path.expanduser('~/.orbstack/config/docker.json')
json.dump(config, open(path, 'w'), indent=2)
print('Written:', path)
"

# Full restart required
orbctl stop && sleep 3 && orbctl start

Important: Use host.internal (OrbStack-specific), NOT 127.0.0.1 (points to VM loopback) and NOT host.docker.internal (may not resolve in all contexts).

Why NOT remove the proxy: When TUN is active, removing the Docker proxy means VM traffic goes directly through the bridge → TUN path, which causes TLS handshake timeouts. The proxy provides a working outbound channel.

2G-3: Removing proxy makes Docker worse (counter-intuitive)

Decision tree:

• docker pull broken → Fix docker.json with host.internal proxy (2G-2)
• docker build broken → Use --network host (2G-1) OR pass --build-arg http_proxy=http://host.internal:1082
• Both broken → Fix both: docker.json + --network host

2G-4: Deploy scripts and container healthchecks probe localhost through proxy

Deploy scripts that curl localhost inside containers or Docker healthchecks that use wget http://localhost will route through the proxy if env vars leak into the container.

Common symptoms:

• Container healthcheck shows (unhealthy) but the app inside is running fine
• wget: can't connect to remote host (127.0.0.1): Connection refused in healthcheck logs (proxy port, not app port)

Root cause: Docker inherits uppercase AND lowercase proxy env vars from the host. Many tools only clear uppercase (HTTP_PROXY=) but forget lowercase (http_proxy=http://127.0.0.1:1082). The healthcheck wget uses lowercase.

Fix in docker-compose.yml — clear BOTH cases:

environment:
  # Must clear both uppercase and lowercase — wget/curl check different vars
  - HTTP_PROXY=
  - HTTPS_PROXY=
  - http_proxy=
  - https_proxy=
  - NO_PROXY=*
  - no_proxy=*

Fix in deploy scripts:

_local_bypass="localhost,127.0.0.1,::1"
export NO_PROXY="${_local_bypass}${NO_PROXY:+,${NO_PROXY}}"
export no_proxy="$NO_PROXY"

# Use 127.0.0.1 instead of localhost in probe URLs (some proxy implementations
# only match exact string "localhost" in no-proxy, not the resolved IP)
curl http://127.0.0.1:3001/health   # ✅ bypasses proxy
curl http://localhost:3001/health    # ❌ may still go through proxy

Verify the fix:

# Docker proxy check (should show proxy + no-proxy)
docker info | grep -iE "proxy|No Proxy"

# Pull test
docker pull --quiet hello-world

# Build test (the real verification)
docker build --network host --no-cache - <<'EOF'
FROM alpine:latest
RUN apk update && echo "BUILD OK"
EOF

# Container env check (no proxy leak)
docker exec <container> env | grep -i proxy
# Expected: all empty or not set

Step 2H: SSH/Git Failing Through a TUN (Connection closed by 198.18.x.x)

Symptom: git clone/fetch/push fails with Connection closed by 198.18.0.x port 443. ssh -T git@github.com may also fail. DNS resolution returns 198.18.x.x addresses instead of real IPs.

First, a warning about this symptom: the 198.18.x.x in the error message is not evidence that fake-IP caused the failure. Under TUN, every hostname resolves to a fake IP, so that address appears in the error whether the connection failed for this reason or any other. It tells you a TUN is active — nothing more. Two very different mechanisms produce an identical error line, and they need opposite fixes:

Tell them apart before doing anything — run the same proxy path with plain HTTPS to an unrelated host, enough times to see a rate rather than an anecdote:

# Same proxy, plain HTTPS, unrelated destination — does it also fail?
for i in $(seq 1 40); do
  curl -s -o /dev/null -x http://127.0.0.1:<proxy-port> \
       -w '%{http_code}\n' -m 10 https://www.google.com/generate_204
done | sort | uniq -c

• Some HTTPS requests fail too (000) at a rate comparable to your SSH failures → (B). The failure is not protocol- or port-specific. Rerouting SSH will not help, because the thing dropping connections is upstream of the protocol.
• HTTPS is 100% clean across many trials while SSH reliably fails → (A), and the DIRECT-rule fix below is warranted.

One measured data point for (B), so the rate is concrete rather than hand-waved: on a macOS host running Shadowrocket in TUN mode, ssh -T git@github.com succeeded 20/20 in a good window and failed roughly 15–20% of attempts in a bad one — while plain HTTPS through the explicit proxy to an unrelated host failed at a comparable rate in the same window. Same-day git push failed twice in a row and then succeeded on the third try, unchanged. That machine was (B), so the port-443 story did not survive contact with the measurement. This is one host, not a universal refutation — run the test above and find out which one you have.

Fix for (B) — retry, and make it automatic. The failure is episodic, so the cheapest correct response is to try again. Make it transparent at git's transport layer rather than remembering to re-run commands:

git config --global core.sshCommand /path/to/ssh-retry-wrapper.sh

Two things that wrapper must get right:

• Only retry failures that happen before key exchange completes. Match on stderr signatures such as kex_exchange_identification, Connection closed|reset by <host> port <n>, and Connection timed out during banner exchange. If key exchange never completed, ssh never ran the remote command, so git received zero protocol bytes and reopening the connection is invisible to it. A mid-transfer drop carries none of those signatures and must pass through untouched — retrying there is what corrupts things.
• Don't reach for ConnectionAttempts instead; it does not work here. It retries only the TCP connect phase, and under TUN the handshake completes locally no matter what the destination does — so connect always "succeeds" and the failure lands afterwards, in the banner exchange. Measured with a listener that accepts and immediately closes: ConnectionAttempts=1, 3, and 5 all produced exactly one accept.

⚠️ Beware stacking retries. If a wrapper script or cron job already retries pushes, adding a transport-layer retry underneath multiplies them (5 × 3 = 15 connections), and the outer layer's logs will undercount actual connection attempts.

Fix for (A) — a DIRECT rule (requires proxy tool config access), so the TUN passes this traffic through without protocol inspection:

IP-CIDR,140.82.112.0/24,DIRECT
IP-CIDR,192.30.252.0/22,DIRECT

This degrades softly: if it doesn't help, you are back where you started.

Not recommended: hardcoding GitHub's IP in ~/.ssh/config. Earlier versions of this skill prescribed HostName 140.82.112.35. Three reasons to avoid it:

1. It goes stale, and fails hard when it does. GitHub rotates these addresses; a dead hardcoded IP surfaces as connection refused, which reads like an outage. Prescribing a weekly cron job to babysit an IP is a sign the fix is in the wrong place.
2. It may not bypass what it claims to. Proxy tools route by rule, not by whether the destination happens to be a fake IP — so unless a matching DIRECT rule exists, a literal IP takes the same forwarding path as the ho

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