logs

Co-authored-by: Matt Van Horn <455140+mvanhorn@users.noreply.github.com>
Co-authored-by: Quentin McGaw <quentin.mcgaw@gmail.com>

Thanks also to @arturhoo for also trying to resolve this issue in #3410

.github/workflows/ci.yml

@@ -67,6 +67,10 @@ jobs:
           -v "$(pwd)/coverage.txt:/tmp/gobuild/coverage.txt" \
           test-container
 
+      - name: Run integration tests in test container
+        run: |
+          docker run --rm --entrypoint go test-container test -tags=integration ./internal/restrictednet
+
       - name: Verify dev cross platform compatibility
         run: docker build --target xcompile .
 
@@ -237,3 +241,5 @@ jobs:
             VERSION=${{ fromJSON(steps.meta.outputs.json).labels['org.opencontainers.image.version'] }}
           tags: ${{ steps.meta.outputs.tags }}
           push: true
+          provenance: mode=max
+          sbom: true

AGENTS.md

@@ -50,6 +50,7 @@ Guidance for coding agents working in this repository.
 - Prefer splitting a code line only when it triggers the `lll` linter, do not split a command or arguments list for each element
 - Use `netip` types instead of `net` types whenever possible
 - Use constants instead of variables whenever possible, especially function-local inline constants.
+- Prefer using pure functions over methods when possible. Especially if the method does not need any fields from the receiving struct, it should be a pure function.
 - Do not use `time.Sleep`, prefer using a `time.Timer` with a `select` statement also listening on a context cancelation
 - `panic`:
   - should only be used when a programming error is encountered and you should NOT return errors for programming errors (such as passing nil objects)
@@ -115,6 +116,7 @@ Mocking works with the `go.uber.org/mock` library, and the `mockgen` tool.
   - **Never** use `.AnyTimes()` on mocks. Always define the number of times a certain mock call should be called, with `.Times(3)` for example.
   - **Always** set the `.Return(...)` on the mock if the function returns something.
   - Avoid using **mock helpers** functions, prefer a bit of repetition than tight coupling and dependency
+  - Always define the gomock controller `ctrl` in the subtest and not in the parent test, or a subtest mock failing will crash all the other subtests.
 
 ### main.go
 
@@ -127,6 +129,7 @@ The Go formatter used is gofumpt.
 ### Errors
 
 - Always prefer wrapping errors with some context with `fmt.Errorf("doing this: %w", err)`
+- Use `errors.New("error message")` when creating a 'bottom' constant string error without additional context, instead of `fmt.Errorf`
 - In rare cases, you can just use `return err` notably:
   - If the function is called **recursively**, since we don't wrap the wrapping multiple times for each recursion
   - If the current function only statement is the call to another function, for example:
@@ -179,6 +182,8 @@ The Go formatter used is gofumpt.
 
 - Do not use `http.DefaultClient`, use a custom `*http.Client` with a fixed timeout and share with dependency injections.
 - Do not check for injected dependencies being `nil`, prefer to just panic on a nil pointer. By default it's fine to panic if a developer injects a dependency `nil`. `nil` does not mean use a default.
+- Prefer using a `switch { case ...}` statement over multiple consecutive `if` statements to have shorter code.
+- Prefer using `[...]T` instead of `[]T` when the length is fixed and known at compile time, to avoid unnecessary allocations.
 
 ## Validation checklist
 

Dockerfile

@@ -3,7 +3,7 @@ ARG GO_ALPINE_VERSION=3.23
 ARG GO_VERSION=1.25
 ARG XCPUTRANSLATE_VERSION=v0.9.0
 ARG GOLANGCI_LINT_VERSION=v2.4.0
-ARG MOCKGEN_VERSION=v1.6.0
+ARG MOCKGEN_VERSION=v0.6.0
 ARG BUILDPLATFORM=linux/amd64
 
 FROM --platform=${BUILDPLATFORM} ghcr.io/qdm12/xcputranslate:${XCPUTRANSLATE_VERSION} AS xcputranslate

go.mod

@@ -56,7 +56,7 @@ require (
 	github.com/prometheus/common v0.60.1 // indirect
 	github.com/prometheus/procfs v0.15.1 // indirect
 	github.com/riobard/go-bloom v0.0.0-20200614022211-cdc8013cb5b3 // indirect
-	golang.org/x/crypto v0.52.0 // indirect
+	golang.org/x/crypto v0.51.0 // indirect
 	golang.org/x/exp v0.0.0-20241009180824-f66d83c29e7c // indirect
 	golang.org/x/mod v0.36.0 // indirect
 	golang.org/x/sync v0.21.0 // indirect

go.sum

@@ -120,8 +120,8 @@ golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACk
 golang.org/x/crypto v0.0.0-20200302210943-78000ba7a073/go.mod h1:LzIPMQfyMNhhGPhUkYOs5KpL4U8rLKemX1yGLhDgUto=
 golang.org/x/crypto v0.0.0-20210921155107-089bfa567519/go.mod h1:GvvjBRRGRdwPK5ydBHafDWAxML/pGHZbMvKqRZ5+Abc=
 golang.org/x/crypto v0.7.0/go.mod h1:pYwdfH91IfpZVANVyUOhSIPZaFoJGxTFbZhFTx+dXZU=
-golang.org/x/crypto v0.52.0 h1:RMs7fP2rXdep0CftQlK8Uf+kibLm7qkCcradZWYz988=
-golang.org/x/crypto v0.52.0/go.mod h1:1QgfPxDqh0T2M/elOJtp9RvuR95kVjir0e6/BvEmGbc=
+golang.org/x/crypto v0.51.0 h1:IBPXwPfKxY7cWQZ38ZCIRPI50YLeevDLlLnyC5wRGTI=
+golang.org/x/crypto v0.51.0/go.mod h1:8AdwkbraGNABw2kOX6YFPs3WM22XqI4EXEd8g+x7Oc8=
 golang.org/x/exp v0.0.0-20241009180824-f66d83c29e7c h1:7dEasQXItcW1xKJ2+gg5VOiBnqWrJc+rq0DPKyvvdbY=
 golang.org/x/exp v0.0.0-20241009180824-f66d83c29e7c/go.mod h1:NQtJDoLvd6faHhE7m4T/1IY708gDefGGjR/iUW8yQQ8=
 golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=

internal/firewall/interfaces.go

@@ -28,6 +28,8 @@ type firewallImpl interface { //nolint:interfacebloat
 	AcceptIpv6MulticastOutput(ctx context.Context, intf string) error
 	AcceptOutput(ctx context.Context, protocol, intf string,
 		ip netip.Addr, port uint16, remove bool) error
+	AcceptOutputFromIPPortToIPPort(ctx context.Context, protocol, intf string,
+		source, destination netip.AddrPort, remove bool) error
 	AcceptOutputFromIPToSubnet(ctx context.Context, intf string, assignedIP netip.Addr,
 		subnet netip.Prefix, remove bool) error
 	AcceptOutputThroughInterface(ctx context.Context, intf string, remove bool) error

internal/firewall/iptables/iptables.go

@@ -2,6 +2,7 @@ package iptables
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"net/netip"
@@ -177,6 +178,29 @@ func (c *Config) AcceptOutput(ctx context.Context,
 	return c.runIP6tablesInstruction(ctx, instruction)
 }
 
+func (c *Config) AcceptOutputFromIPPortToIPPort(ctx context.Context,
+	protocol, intf string, source, destination netip.AddrPort, remove bool,
+) error {
+	if source.Addr().BitLen() != destination.Addr().BitLen() {
+		return errors.New("source and destination address families do not match")
+	}
+
+	interfaceFlag := "-o " + intf
+	if intf == "*" { // all interfaces
+		interfaceFlag = ""
+	}
+
+	instruction := fmt.Sprintf("%s OUTPUT %s -s %s -d %s -p %s -m %s --sport %d --dport %d -j ACCEPT",
+		appendOrDelete(remove), interfaceFlag, source.Addr(), destination.Addr(),
+		protocol, protocol, source.Port(), destination.Port())
+	if destination.Addr().Is4() {
+		return c.runIptablesInstruction(ctx, instruction)
+	} else if c.ip6Tables == "" {
+		return fmt.Errorf("accept output from %s to %s: %s", source, destination, needIP6Tables)
+	}
+	return c.runIP6tablesInstruction(ctx, instruction)
+}
+
 // AcceptOutputFromIPToSubnet accepts outgoing traffic from sourceIP to destinationSubnet
 // on the interface intf. If intf is empty, it is set to "*" which means all interfaces.
 // If remove is true, the rule is removed instead of added.

internal/firewall/wrappers.go

@@ -25,3 +25,10 @@ func (c *Config) AcceptOutput(ctx context.Context, protocol, intf string,
 ) error {
 	return c.impl.AcceptOutput(ctx, protocol, intf, ip, port, remove)
 }
+
+func (c *Config) AcceptOutputFromIPPortToIPPort(ctx context.Context,
+	protocol, intf string, source, destination netip.AddrPort, remove bool,
+) error {
+	return c.impl.AcceptOutputFromIPPortToIPPort(ctx, protocol, intf,
+		source, destination, remove)
+}

internal/healthcheck/checker.go

@@ -8,7 +8,6 @@ import (
 	"net"
 	"net/netip"
 	"strings"
-	"sync"
 	"time"
 
 	"github.com/qdm12/gluetun/internal/healthcheck/dns"
@@ -24,7 +23,6 @@ type Checker struct {
 	icmpTargetIPs  []netip.Addr
 	smallCheckType string
 	startupOnFail  bool
-	configMutex    sync.Mutex
 
 	icmpNotPermitted *bool
 
@@ -55,8 +53,6 @@ func NewChecker(logger Logger) *Checker {
 func (c *Checker) SetConfig(tlsDialAddrs []string, icmpTargets []netip.Addr,
 	smallCheckType string, startupOnFail bool,
 ) {
-	c.configMutex.Lock()
-	defer c.configMutex.Unlock()
 	c.tlsDialAddrs = tlsDialAddrs
 	c.icmpTargetIPs = icmpTargets
 	c.smallCheckType = smallCheckType
@@ -166,10 +162,8 @@ func (c *Checker) Stop() error {
 }
 
 func (c *Checker) smallPeriodicCheck(ctx context.Context) error {
-	c.configMutex.Lock()
 	icmpTargetIPs := make([]netip.Addr, len(c.icmpTargetIPs))
 	copy(icmpTargetIPs, c.icmpTargetIPs)
-	c.configMutex.Unlock()
 	tryTimeouts := []time.Duration{
 		5 * time.Second,
 		5 * time.Second,

internal/portforward/loop.go

@@ -99,6 +99,7 @@ func (l *Loop) run(runCtx context.Context, runDone chan<- struct{},
 		case partialUpdate := <-updateTrigger:
 			updatedSettings, err := l.settings.updateWith(partialUpdate, *l.settings.VPNIsUp)
 			if err != nil {
+				l.logger.Debug(fmt.Sprintf("port forward loop: run: updateWith error %v", err))
 				updateResult <- err
 				continue
 			}
@@ -136,6 +137,7 @@ func (l *Loop) run(runCtx context.Context, runDone chan<- struct{},
 			if err != nil {
 				err = fmt.Errorf("starting port forwarding service: %w", err)
 			}
+			l.logger.Debug(fmt.Sprintf("port forward loop: Start: error is %v", err))
 			updateResult <- err
 		} else if err != nil {
 			// Log the error and schedule a retry
@@ -150,6 +152,7 @@ func (l *Loop) UpdateWith(partialUpdate Settings) (err error) {
 	case l.updateTrigger <- partialUpdate:
 		select {
 		case err = <-l.updatedResult:
+			l.logger.Debug(fmt.Sprintf("port forward loop: UpdateWith: received error %v", err))
 			return err
 		case <-l.runCtx.Done():
 			return l.runCtx.Err()

internal/portforward/service/start.go

@@ -123,7 +123,9 @@ func (s *Service) onNewPorts(ctx context.Context, internalToExternalPorts map[ui
 		}
 	}
 
+	s.logger.Debug(fmt.Sprintf("writePortForwardedFile with externalPorts: %v", externalPorts))
 	err = s.writePortForwardedFile(externalPorts)
+	s.logger.Debug(fmt.Sprintf("writing port file: error is %v", err))
 	if err != nil {
 		_ = s.cleanup()
 		return fmt.Errorf("writing port file: %w", err)

internal/portforward/service/stop.go

@@ -58,6 +58,7 @@ func (s *Service) cleanup() (err error) {
 
 	s.ports = nil
 
+	s.logger.Debug("writePortForwardedFile in cleanup")
 	err = s.writePortForwardedFile(nil)
 	if err != nil {
 		return fmt.Errorf("clearing port file: %w", err)

internal/provider/protonvpn/portforward.go

@@ -133,6 +133,20 @@ func (p *Provider) KeepPortForward(ctx context.Context,
 		case <-timer.C:
 		}
 
+		_, externalIPv4Address, err := client.ExternalAddress(ctx, objects.Gateway)
+		if err != nil {
+			switch {
+			case strings.HasSuffix(err.Error(), "connection refused"):
+				err = fmt.Errorf("%w - make sure you have +pmp at the end of your OpenVPN username "+
+					"or that your Wireguard key is set to work with PMP", err)
+			case strings.Contains(err.Error(), "i/o timeout"):
+				err = fmt.Errorf("%w - make sure FIREWALL_OUTBOUND_SUBNETS does not conflict with "+
+					"the VPN gateway ip address %s", err, objects.Gateway)
+			}
+			logger.Error(fmt.Sprintf("getting external IPv4 address: %v", err))
+		}
+		logger.Debug("gateway external IPv4 address is " + externalIPv4Address.String())
+
 		objects.Logger.Debug("refreshing forwarded ports since 45 seconds have elapsed")
 		const lifetime = 60 * time.Second
 		for internalPort, externalPort := range p.internalToExternalPorts {

internal/restrictednet/client.go

@@ -0,0 +1,82 @@
+package restrictednet
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net"
+	"net/http"
+	"net/netip"
+	"strconv"
+
+	"github.com/qdm12/dns/v2/pkg/provider"
+)
+
+// Client is a client for making restricted network requests,
+// such as opening temporary firewall rules for HTTPS connections.
+// It is not meant to be high performance, although it can be used for
+// multiple requests and concurrently.
+type Client struct {
+	outboundInterface string
+	ipv6Supported     bool
+	firewall          Firewall
+	dohServers        []provider.DoHServer
+}
+
+func New(settings Settings) *Client {
+	if err := settings.validate(); err != nil {
+		panic(fmt.Sprintf("invalid settings: %v", err)) // programming error
+	}
+	dohServers := make([]provider.DoHServer, len(settings.UpstreamResolvers))
+	for i, upstreamResolver := range settings.UpstreamResolvers {
+		dohServers[i] = upstreamResolver.DoH
+	}
+
+	return &Client{
+		outboundInterface: settings.DefaultInterface,
+		ipv6Supported:     *settings.IPv6Supported,
+		firewall:          settings.Firewall,
+		dohServers:        dohServers,
+	}
+}
+
+// OpenHTTPSByHostname opens an https connection through the firewall,
+// to the hostname which in the format `host:port`. The returned cleanup
+// function must be called to remove the temporary firewall rule and close connections.
+// It first resolves the domain in hostname using DNS over HTTPS and then opens
+// the restricted HTTPS connection to the resolved IP.
+func (c *Client) OpenHTTPSByHostname(ctx context.Context, hostname string) (
+	httpClient *http.Client, cleanup func() error, err error,
+) {
+	host, portStr, err := net.SplitHostPort(hostname)
+	if err != nil {
+		return nil, nil, fmt.Errorf("splitting host and port: %w", err)
+	}
+	resolvedIPs, err := c.ResolveName(ctx, host)
+	if err != nil {
+		return nil, nil, fmt.Errorf("resolving name: %w", err)
+	} else if len(resolvedIPs) == 0 {
+		return nil, nil, fmt.Errorf("no IP address found for name %q", host)
+	}
+
+	portUint, err := strconv.ParseUint(portStr, 10, 16)
+	if err != nil {
+		return nil, nil, fmt.Errorf("parsing port: %w", err)
+	} else if portUint == 0 {
+		return nil, nil, errors.New("destination port cannot be 0")
+	}
+	port := uint16(portUint)
+
+	errs := make([]error, 0, len(resolvedIPs))
+	for _, ip := range resolvedIPs {
+		addrPort := netip.AddrPortFrom(ip, port)
+		httpClient, cleanup, err := c.OpenHTTPS(ctx, host, addrPort)
+		if err != nil {
+			errs = append(errs, fmt.Errorf("for %s: %w", ip, err))
+			continue
+		}
+		return httpClient, cleanup, nil
+	}
+
+	return nil, nil, fmt.Errorf("opening HTTPS to %s: %w", hostname, errors.Join(errs...))
+}

internal/restrictednet/helpers_test.go

@@ -0,0 +1,7 @@
+//go:build integration
+
+package restrictednet
+
+func ptrTo[T any](value T) *T {
+	return &value
+}

internal/restrictednet/https.go

@@ -0,0 +1,202 @@
+package restrictednet
+
+import (
+	"context"
+	"crypto/tls"
+	"errors"
+	"fmt"
+	"net"
+	"net/http"
+	"net/netip"
+	"os"
+	"time"
+
+	"github.com/jsimonetti/rtnetlink"
+	"github.com/qdm12/gluetun/internal/pmtud/constants"
+)
+
+// OpenHTTPS opens temporary restrictive firewall output for one HTTPS destination.
+// The returned [*http.Client] must be used sequentially only, and each request must
+// have its response body fully read/discarded and then closed.
+// The returned cleanup function must be called to remove the temporary firewall rule and close connections.
+func (c *Client) OpenHTTPS(ctx context.Context, destinationTLSName string, destinationAddrPort netip.AddrPort,
+) (httpClient *http.Client, cleanup func() error, err error) {
+	fd, sourceAddrPort, err := bindSourceConnection(destinationAddrPort.Addr())
+	if err != nil {
+		return nil, nil, fmt.Errorf("binding source port: %w", err)
+	}
+
+	const remove = false
+	err = c.firewall.AcceptOutputFromIPPortToIPPort(ctx, "tcp", c.outboundInterface,
+		sourceAddrPort, destinationAddrPort, remove)
+	if err != nil {
+		closeFD(fd)
+		return nil, nil, fmt.Errorf("allowing output traffic through firewall: %w", err)
+	}
+
+	connection, err := connectSourceConnection(ctx, fd, destinationAddrPort)
+	if err != nil {
+		const remove = true
+		_ = c.firewall.AcceptOutputFromIPPortToIPPort(context.Background(), "tcp", c.outboundInterface,
+			sourceAddrPort, destinationAddrPort, remove)
+		return nil, nil, fmt.Errorf("connecting source socket: %w", err)
+	}
+
+	dial := makeDial(connection, destinationTLSName)
+	httpClient = newHTTPSClient(destinationTLSName, dial)
+	cleanup = func() error {
+		var errs []error
+		httpClient.CloseIdleConnections()
+		err := connection.Close()
+		if err != nil && !errors.Is(err, net.ErrClosed) {
+			errs = append(errs, fmt.Errorf("closing connection: %w", err))
+		}
+		const remove = true
+		err = c.firewall.AcceptOutputFromIPPortToIPPort(context.Background(), "tcp", c.outboundInterface,
+			sourceAddrPort, destinationAddrPort, remove)
+		if err != nil {
+			errs = append(errs, fmt.Errorf("removing output traffic rule: %w", err))
+		}
+		if len(errs) > 0 {
+			return errors.Join(errs...)
+		}
+		return nil
+	}
+	return httpClient, cleanup, nil
+}
+
+type dialFunc func(ctx context.Context, network, address string) (net.Conn, error)
+
+func newHTTPSClient(destinationTLSName string, dial dialFunc) *http.Client {
+	const timeout = 5 * time.Second
+	transport := &http.Transport{
+		MaxIdleConns:        1,
+		MaxIdleConnsPerHost: 1,
+		MaxConnsPerHost:     1,
+		TLSClientConfig: &tls.Config{
+			MinVersion: tls.VersionTLS12,
+			ServerName: destinationTLSName,
+		},
+		DialContext: dial,
+	}
+	return &http.Client{
+		Timeout:   timeout,
+		Transport: transport,
+	}
+}
+
+func makeDial(connection net.Conn, tlsName string) dialFunc {
+	_, destinationPort, err := net.SplitHostPort(connection.RemoteAddr().String())
+	if err != nil {
+		panic(err) // connection remote address should always be in the form "host:port"
+	}
+	expectedAddress := net.JoinHostPort(tlsName, destinationPort)
+	used := false
+	return func(_ context.Context, network, address string) (net.Conn, error) {
+		if used {
+			return nil, errors.New("dial function called more than once")
+		}
+		used = true
+		switch network {
+		case "tcp", "tcp4", "tcp6":
+		default:
+			return nil, fmt.Errorf("unexpected dial network %q", network)
+		}
+		if address != expectedAddress {
+			return nil, fmt.Errorf("unexpected dial address %q (expected %q)", address, expectedAddress)
+		}
+		return connection, nil
+	}
+}
+
+func bindSourceConnection(destinationIP netip.Addr) (fd int, sourceAddr netip.AddrPort, err error) {
+	sourceIP, err := sourceIPForDestination(destinationIP)
+	if err != nil {
+		return 0, netip.AddrPort{}, fmt.Errorf("finding source IP: %w", err)
+	}
+
+	family := constants.AF_INET
+	if sourceIP.Is6() {
+		family = constants.AF_INET6
+	}
+
+	fd, err = newTCPSockStream(family)
+	if err != nil {
+		return 0, netip.AddrPort{}, fmt.Errorf("creating socket: %w", err)
+	}
+
+	bindAddrPort := netip.AddrPortFrom(sourceIP, 0)
+	err = bindFD(fd, bindAddrPort)
+	if err != nil {
+		closeFD(fd)
+		return 0, netip.AddrPort{}, fmt.Errorf("binding socket: %w", err)
+	}
+
+	sourceAddr, err = fdToSourceAddr(fd)
+	if err != nil {
+		closeFD(fd)
+		return 0, netip.AddrPort{}, fmt.Errorf("getting source address: %w", err)
+	}
+
+	return fd, sourceAddr, nil
+}
+
+func connectSourceConnection(ctx context.Context, fd int, destinationAddrPort netip.AddrPort) (
+	connection net.Conn, err error,
+) {
+	err = connectFD(ctx, fd, destinationAddrPort)
+	if err != nil {
+		closeFD(fd)
+		return nil, fmt.Errorf("connecting socket: %w", err)
+	}
+
+	file := os.NewFile(uintptr(fd), "")
+	if file == nil {
+		closeFD(fd)
+		return nil, fmt.Errorf("creating socket file for destination %s", destinationAddrPort)
+	}
+	defer file.Close()
+
+	connection, err = net.FileConn(file)
+	if err != nil {
+		return nil, fmt.Errorf("wrapping socket connection: %w", err)
+	}
+
+	return connection, nil
+}
+
+func sourceIPForDestination(destinationIP netip.Addr) (srcIP netip.Addr, err error) {
+	conn, err := rtnetlink.Dial(nil)
+	if err != nil {
+		return netip.Addr{}, err
+	}
+	defer conn.Close()
+
+	family := uint8(constants.AF_INET)
+	if destinationIP.Is6() {
+		family = constants.AF_INET6
+	}
+
+	requestMessage := &rtnetlink.RouteMessage{
+		Family: family,
+		Attributes: rtnetlink.RouteAttributes{
+			Dst: destinationIP.AsSlice(),
+		},
+	}
+	messages, err := conn.Route.Get(requestMessage)
+	if err != nil {
+		return netip.Addr{}, fmt.Errorf("getting routes to %s: %w", destinationIP, err)
+	}
+
+	for _, message := range messages {
+		if message.Attributes.Src == nil {
+			continue
+		}
+		if message.Attributes.Src.To4() == nil {
+			return netip.AddrFrom16([16]byte(message.Attributes.Src)), nil
+		}
+		return netip.AddrFrom4([4]byte(message.Attributes.Src)), nil
+	}
+
+	return netip.Addr{}, fmt.Errorf("no route to %s", destinationIP)
+}

internal/restrictednet/https_integration_test.go

@@ -0,0 +1,117 @@
+//go:build integration
+
+package restrictednet
+
+import (
+	"context"
+	"fmt"
+	"io"
+	"net/http"
+	"net/netip"
+	"testing"
+
+	"github.com/qdm12/dns/v2/pkg/provider"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/mock/gomock"
+)
+
+type listenAddrPortMatcher struct {
+	expected netip.AddrPort
+}
+
+func (m listenAddrPortMatcher) Matches(x any) bool {
+	ip, ok := x.(netip.AddrPort)
+	if !ok {
+		return false
+	}
+	if m.expected.IsValid() {
+		return ip == m.expected
+	}
+	return ip.IsValid() && ip.Addr().IsValid() && ip.Port() > 0
+}
+
+func (m listenAddrPortMatcher) String() string {
+	if m.expected.IsValid() {
+		return "is the same as " + m.expected.String()
+	}
+	return "is a valid netip.AddrPort with a valid IP and non-zero port"
+}
+
+type destinationAddrPortMatcher struct {
+	expected netip.AddrPort
+}
+
+func (m destinationAddrPortMatcher) Matches(x any) bool {
+	ip, ok := x.(netip.AddrPort)
+	if !ok {
+		return false
+	}
+	if m.expected.IsValid() {
+		return ip == m.expected
+	}
+	return ip.IsValid() && ip.Port() == m.expected.Port()
+}
+
+func (m destinationAddrPortMatcher) String() string {
+	if m.expected.IsValid() {
+		return "is the same as " + m.expected.String()
+	}
+	return "matches the port " + fmt.Sprint(m.expected.Port())
+}
+
+func Test_Client_OpenHTTPS(t *testing.T) {
+	t.Parallel()
+	ctx := t.Context()
+	ctrl := gomock.NewController(t)
+
+	const destinationTLSName = "one.one.one.one"
+	destinationAddrPort := netip.AddrPortFrom(netip.AddrFrom4([4]byte{1, 1, 1, 1}), 443)
+
+	firewall := NewMockFirewall(ctrl)
+	sourceMatcher := listenAddrPortMatcher{}
+	firewall.EXPECT().AcceptOutputFromIPPortToIPPort(
+		ctx, "tcp", "eth0", sourceMatcher, destinationAddrPort, false,
+	).DoAndReturn(func(_ context.Context,
+		_, _ string, source, _ netip.AddrPort, _ bool,
+	) error {
+		sourceMatcher.expected = source
+		return nil
+	})
+	firewall.EXPECT().AcceptOutputFromIPPortToIPPort(
+		context.Background(), "tcp", "eth0", sourceMatcher, destinationAddrPort, true,
+	).Return(nil)
+
+	const ipv6Supported = false
+	upstreamResolvers := []provider.Provider{provider.Google()}
+	settings := Settings{
+		Firewall:          firewall,
+		DefaultInterface:  "eth0",
+		IPv6Supported:     ptrTo(ipv6Supported),
+		UpstreamResolvers: upstreamResolvers,
+	}
+	client := New(settings)
+
+	httpClient, cleanup, err := client.OpenHTTPS(ctx, destinationTLSName, destinationAddrPort)
+	require.NoError(t, err)
+	require.NotNil(t, httpClient)
+	require.NotNil(t, cleanup)
+
+	const requests = 2
+
+	for range requests {
+		request, err := http.NewRequestWithContext(ctx, http.MethodGet, "https://"+destinationTLSName, nil)
+		require.NoError(t, err)
+
+		response, err := httpClient.Do(request)
+		require.NoError(t, err)
+		_, err = io.Copy(io.Discard, response.Body)
+		require.NoError(t, err)
+		err = response.Body.Close()
+		require.NoError(t, err)
+		assert.Equal(t, http.StatusOK, response.StatusCode)
+	}
+
+	err = cleanup()
+	require.NoError(t, err)
+}

internal/restrictednet/interfaces.go

@@ -0,0 +1,12 @@
+package restrictednet
+
+import (
+	"context"
+	"net/netip"
+)
+
+type Firewall interface {
+	AcceptOutputFromIPPortToIPPort(ctx context.Context,
+		protocol, intf string, source, destination netip.AddrPort, remove bool,
+	) error
+}

internal/restrictednet/linux.go

@@ -0,0 +1,121 @@
+//go:build linux
+
+package restrictednet
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net/netip"
+	"time"
+
+	"golang.org/x/sys/unix"
+)
+
+func closeFD(fd int) {
+	unix.Close(fd)
+}
+
+func newTCPSockStream(family int) (fd int, err error) {
+	fd, err = unix.Socket(family, unix.SOCK_STREAM, unix.IPPROTO_TCP)
+	if err != nil {
+		return 0, err
+	}
+	err = unix.SetNonblock(fd, true)
+	if err != nil {
+		_ = unix.Close(fd)
+		return 0, err
+	}
+	return fd, nil
+}
+
+func bindFD(fd int, address netip.AddrPort) error {
+	bindAddr := makeSockAddr(address)
+	return unix.Bind(fd, bindAddr)
+}
+
+func connectFD(ctx context.Context, fd int, destination netip.AddrPort) error {
+	err := unix.Connect(fd, makeSockAddr(destination))
+	switch {
+	case err == nil:
+		return nil
+	case !errors.Is(err, unix.EINPROGRESS):
+		return err
+	}
+
+	for {
+		select {
+		case <-ctx.Done():
+			return ctx.Err()
+		default:
+			bitsIndex := fd / 64 //nolint:mnd
+			if bitsIndex >= len(unix.FdSet{}.Bits) {
+				return fmt.Errorf("fd %d exceeds unix.Select FdSet capacity", fd)
+			}
+			wset := &unix.FdSet{}
+			wset.Bits[bitsIndex] |= 1 << (uint64(fd) % 64) //nolint:gosec,mnd
+			eset := &unix.FdSet{}
+			eset.Bits[bitsIndex] |= 1 << (uint64(fd) % 64) //nolint:gosec,mnd
+			const selectTimeout = 50 * time.Millisecond
+			timeval := unix.NsecToTimeval(int64(selectTimeout))
+
+			// Wait for the FD to become writable or hit an error state
+			n, err := unix.Select(fd+1, nil, wset, eset, &timeval)
+			if err != nil {
+				if errors.Is(err, unix.EINTR) {
+					continue // Syscall interrupted, try again
+				}
+				return fmt.Errorf("select error: %w", err)
+			} else if n == 0 {
+				continue // no status change yet
+			}
+
+			// Check if the socket encountered an error
+			n, err = unix.GetsockoptInt(fd, unix.SOL_SOCKET, unix.SO_ERROR)
+			if err != nil {
+				return fmt.Errorf("getsockopt error: %w", err)
+			} else if n != 0 {
+				return fmt.Errorf("connect failed asynchronously: %w", unix.Errno(n))
+			}
+
+			return nil
+		}
+	}
+}
+
+func fdToSourceAddr(fd int) (sourceAddrPort netip.AddrPort, err error) {
+	sockAddr, err := unix.Getsockname(fd)
+	if err != nil {
+		return netip.AddrPort{}, fmt.Errorf("getting sockname: %w", err)
+	}
+
+	sourceAddrPort, err = sockAddrToAddrPort(sockAddr)
+	if err != nil {
+		return netip.AddrPort{}, err
+	}
+	return sourceAddrPort, nil
+}
+
+func makeSockAddr(addressPort netip.AddrPort) unix.Sockaddr {
+	if addressPort.Addr().Is4() {
+		return &unix.SockaddrInet4{
+			Port: int(addressPort.Port()),
+			Addr: addressPort.Addr().As4(),
+		}
+	}
+	return &unix.SockaddrInet6{
+		Port: int(addressPort.Port()),
+		Addr: addressPort.Addr().As16(),
+	}
+}
+
+func sockAddrToAddrPort(sockAddr unix.Sockaddr) (addrPort netip.AddrPort, err error) {
+	switch typedSockAddr := sockAddr.(type) {
+	case *unix.SockaddrInet4:
+		return netip.AddrPortFrom(netip.AddrFrom4(typedSockAddr.Addr), uint16(typedSockAddr.Port)), nil //nolint:gosec
+	case *unix.SockaddrInet6:
+		return netip.AddrPortFrom(netip.AddrFrom16(typedSockAddr.Addr), uint16(typedSockAddr.Port)), nil //nolint:gosec
+	default:
+		return netip.AddrPort{}, fmt.Errorf("unexpected socket address type %T", typedSockAddr)
+	}
+}

internal/restrictednet/mocks_generate_test.go

@@ -0,0 +1,3 @@
+package restrictednet
+
+//go:generate mockgen -destination=mocks_test.go -package=$GOPACKAGE . Firewall

internal/restrictednet/mocks_test.go

@@ -0,0 +1,56 @@
+// Code generated by MockGen. DO NOT EDIT.
+// Source: github.com/qdm12/gluetun/internal/restrictednet (interfaces: Firewall)
+//
+// Generated by this command:
+//
+//	mockgen -destination=mocks_test.go -package=restrictednet . Firewall
+//
+
+// Package restrictednet is a generated GoMock package.
+package restrictednet
+
+import (
+	context "context"
+	netip "net/netip"
+	reflect "reflect"
+
+	gomock "go.uber.org/mock/gomock"
+)
+
+// MockFirewall is a mock of Firewall interface.
+type MockFirewall struct {
+	ctrl     *gomock.Controller
+	recorder *MockFirewallMockRecorder
+	isgomock struct{}
+}
+
+// MockFirewallMockRecorder is the mock recorder for MockFirewall.
+type MockFirewallMockRecorder struct {
+	mock *MockFirewall
+}
+
+// NewMockFirewall creates a new mock instance.
+func NewMockFirewall(ctrl *gomock.Controller) *MockFirewall {
+	mock := &MockFirewall{ctrl: ctrl}
+	mock.recorder = &MockFirewallMockRecorder{mock}
+	return mock
+}
+
+// EXPECT returns an object that allows the caller to indicate expected use.
+func (m *MockFirewall) EXPECT() *MockFirewallMockRecorder {
+	return m.recorder
+}
+
+// AcceptOutputFromIPPortToIPPort mocks base method.
+func (m *MockFirewall) AcceptOutputFromIPPortToIPPort(ctx context.Context, protocol, intf string, source, destination netip.AddrPort, remove bool) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "AcceptOutputFromIPPortToIPPort", ctx, protocol, intf, source, destination, remove)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// AcceptOutputFromIPPortToIPPort indicates an expected call of AcceptOutputFromIPPortToIPPort.
+func (mr *MockFirewallMockRecorder) AcceptOutputFromIPPortToIPPort(ctx, protocol, intf, source, destination, remove any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "AcceptOutputFromIPPortToIPPort", reflect.TypeOf((*MockFirewall)(nil).AcceptOutputFromIPPortToIPPort), ctx, protocol, intf, source, destination, remove)
+}

internal/restrictednet/notlinux.go

@@ -0,0 +1,28 @@
+//go:build !linux
+
+package restrictednet
+
+import (
+	"context"
+	"net/netip"
+)
+
+func closeFD(fd int) {
+	panic("not implemented")
+}
+
+func newTCPSockStream(family int) (fd int, err error) {
+	panic("not implemented")
+}
+
+func bindFD(fd int, address netip.AddrPort) error {
+	panic("not implemented")
+}
+
+func connectFD(ctx context.Context, fd int, destination netip.AddrPort) error {
+	panic("not implemented")
+}
+
+func fdToSourceAddr(fd int) (sourceAddrPort netip.AddrPort, err error) {
+	panic("not implemented")
+}

internal/restrictednet/resolve.go

@@ -0,0 +1,201 @@
+package restrictednet
+
+import (
+	"bytes"
+	"context"
+	"errors"
+	"fmt"
+	"io"
+	"net/http"
+	"net/netip"
+	"net/url"
+	"strconv"
+
+	"github.com/miekg/dns"
+)
+
+// ResolveName resolves the given host name to IP addresses using DoH servers,
+// while opening temporary restrictive firewall rules for HTTPS traffic to DoH servers.
+// The host must be a single well-formed domain name, without port or path.
+func (c *Client) ResolveName(ctx context.Context, host string) (
+	resolvedAddresses []netip.Addr, err error,
+) {
+	const maxTypes = 2
+	questionTypes := make([]uint16, 0, maxTypes)
+	if c.ipv6Supported {
+		questionTypes = append(questionTypes, dns.TypeAAAA)
+	}
+	questionTypes = append(questionTypes, dns.TypeA)
+
+	var addresses []netip.Addr
+	errs := make([]error, 0, len(questionTypes))
+	for _, questionType := range questionTypes {
+		answerAddresses, err := c.resolveOneQuestionType(ctx, host, questionType)
+		if err != nil {
+			errs = append(errs, err)
+			continue
+		}
+		addresses = append(addresses, answerAddresses...)
+	}
+
+	switch {
+	case len(addresses) > 0:
+		return addresses, nil
+	case len(errs) == 0:
+		return nil, nil // no address found
+	default: // errors
+		return nil, fmt.Errorf("resolving host %q: %w", host, errors.Join(errs...))
+	}
+}
+
+func (c *Client) resolveOneQuestionType(ctx context.Context,
+	host string, questionType uint16,
+) (addresses []netip.Addr, err error) {
+	queryMessage := &dns.Msg{}
+	queryMessage.SetQuestion(dns.Fqdn(host), questionType)
+	queryWire, err := queryMessage.Pack()
+	if err != nil {
+		return nil, fmt.Errorf("packing DNS query: %w", err)
+	}
+
+	// Try every DoH server and every of each of their IP until we get a non-empty
+	// successful response.
+	errs := make([]error, 0)
+	for _, dohServer := range c.dohServers {
+		dohURL, err := url.Parse(dohServer.URL)
+		if err != nil {
+			errs = append(errs,
+				fmt.Errorf("parsing DoH server URL %s: %w", dohServer.URL, err))
+			continue
+		}
+
+		dohServerIPs := make([]netip.Addr, 0, len(dohServer.IPv4)+len(dohServer.IPv6))
+		if c.ipv6Supported {
+			// Prefer IPv6 addresses if IPv6 is supported
+			dohServerIPs = append(dohServerIPs, dohServer.IPv6...)
+		}
+		dohServerIPs = append(dohServerIPs, dohServer.IPv4...)
+
+		for _, dohServerIP := range dohServerIPs {
+			const defaultDoHPort uint16 = 443
+			port := defaultDoHPort
+			if portStr := dohURL.Port(); portStr != "" {
+				port, err = parseDestinationPort(portStr)
+				if err != nil {
+					errs = append(errs, fmt.Errorf("parsing DoH server port: %w", err))
+					continue
+				}
+			}
+			dohServerAddrPort := netip.AddrPortFrom(dohServerIP, port)
+			responseMessage, err := c.doHQuery(ctx, queryWire, dohURL, dohServerAddrPort)
+			switch {
+			case err != nil:
+				errs = append(errs, fmt.Errorf("querying DoH server %q (%s): %w",
+					dohServer.URL, dohServerAddrPort, err))
+				continue
+			case responseMessage.Rcode != dns.RcodeSuccess:
+				errs = append(errs, fmt.Errorf("querying DoH server %q (%s): DNS rcode %s",
+					dohServer.URL, dohServerAddrPort, dns.RcodeToString[responseMessage.Rcode]))
+				continue
+			}
+			addresses := answersToNetipAddrs(responseMessage)
+			if len(addresses) == 0 {
+				continue
+			}
+			return addresses, nil
+		}
+	}
+
+	if len(errs) == 0 {
+		return nil, nil
+	}
+
+	return nil, fmt.Errorf("resolving %s %s: %w",
+		dns.TypeToString[questionType], host, errors.Join(errs...))
+}
+
+func (c *Client) doHQuery(ctx context.Context, queryWire []byte,
+	dohURL *url.URL, dohServerAddrPort netip.AddrPort,
+) (responseMessage *dns.Msg, err error) {
+	httpClient, cleanup, err := c.OpenHTTPS(ctx, dohURL.Hostname(), dohServerAddrPort)
+	if err != nil {
+		return nil, fmt.Errorf("opening https connection: %w", err)
+	}
+	defer func() {
+		closeErr := cleanup()
+		if err == nil && closeErr != nil {
+			err = fmt.Errorf("cleaning up https connection: %w", closeErr)
+		}
+	}()
+
+	requestBody := bytes.NewReader(queryWire)
+	request, err := http.NewRequestWithContext(ctx, http.MethodPost, dohURL.String(), requestBody)
+	if err != nil {
+		return nil, fmt.Errorf("creating request: %w", err)
+	}
+	request.Header.Set("Content-Type", "application/dns-message")
+	request.Header.Set("Accept", "application/dns-message")
+
+	response, err := httpClient.Do(request)
+	if err != nil {
+		return nil, err
+	}
+
+	responseData, err := io.ReadAll(response.Body)
+	if err != nil {
+		_ = response.Body.Close()
+		return nil, fmt.Errorf("reading response body: %w", err)
+	}
+
+	err = response.Body.Close()
+	if err != nil {
+		return nil, fmt.Errorf("closing response body: %w", err)
+	}
+
+	if response.StatusCode != http.StatusOK {
+		return nil, fmt.Errorf("response status code is %s (data length %d)",
+			response.Status, len(responseData))
+	}
+
+	responseMessage = new(dns.Msg)
+	err = responseMessage.Unpack(responseData)
+	if err != nil {
+		return nil, fmt.Errorf("parsing DoH response: %w", err)
+	}
+
+	return responseMessage, nil
+}
+
+func answersToNetipAddrs(message *dns.Msg) (addresses []netip.Addr) {
+	if message == nil {
+		return nil
+	}
+	addresses = make([]netip.Addr, 0, len(message.Answer))
+	for _, answer := range message.Answer {
+		switch record := answer.(type) {
+		case *dns.A:
+			address, ok := netip.AddrFromSlice(record.A)
+			if ok {
+				addresses = append(addresses, address.Unmap())
+			}
+		case *dns.AAAA:
+			address, ok := netip.AddrFromSlice(record.AAAA)
+			if ok {
+				addresses = append(addresses, address)
+			}
+		}
+	}
+	return addresses
+}
+
+func parseDestinationPort(portStr string) (port uint16, err error) {
+	portUint, err := strconv.ParseUint(portStr, 10, 16)
+	if err != nil {
+		return 0, err
+	}
+
+	if portUint == 0 {
+		return 0, errors.New("port cannot be 0")
+	}
+	return uint16(portUint), nil
+}

internal/restrictednet/resolve_integration_test.go

@@ -0,0 +1,110 @@
+//go:build integration
+
+package restrictednet
+
+import (
+	"context"
+	"net"
+	"net/netip"
+	"testing"
+
+	"github.com/miekg/dns"
+	"github.com/qdm12/dns/v2/pkg/provider"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"go.uber.org/mock/gomock"
+)
+
+func Test_Client_ResolveName(t *testing.T) {
+	t.Parallel()
+	ctx := t.Context()
+	ctrl := gomock.NewController(t)
+
+	firewall := NewMockFirewall(ctrl)
+	sourceMatcher := listenAddrPortMatcher{}
+	destinationMatcher := destinationAddrPortMatcher{
+		expected: netip.AddrPortFrom(netip.Addr{}, 443),
+	}
+
+	// Add rule
+	firstCall := firewall.EXPECT().AcceptOutputFromIPPortToIPPort(
+		ctx, "tcp", "eth0", sourceMatcher, destinationMatcher, false,
+	).DoAndReturn(func(
+		_ context.Context, _, _ string, source, destination netip.AddrPort, _ bool,
+	) error {
+		sourceMatcher.expected = source
+		destinationMatcher.expected = destination
+		return nil
+	})
+
+	// Removal rule
+	firewall.EXPECT().AcceptOutputFromIPPortToIPPort(
+		context.Background(), "tcp", "eth0", sourceMatcher, destinationMatcher, true,
+	).Return(nil).After(firstCall)
+
+	settings := Settings{
+		DefaultInterface:  "eth0",
+		IPv6Supported:     ptrTo(false),
+		Firewall:          firewall,
+		UpstreamResolvers: []provider.Provider{provider.Cloudflare()},
+	}
+	client := New(settings)
+
+	addresses, err := client.ResolveName(ctx, "github.com")
+	require.NoError(t, err)
+	assert.NotEmpty(t, addresses)
+}
+
+func Test_answersToNetipAddrs(t *testing.T) {
+	t.Parallel()
+
+	testCases := map[string]struct {
+		message  *dns.Msg
+		expected []netip.Addr
+	}{
+		"nil_message": {},
+		"no_answers": {
+			message:  &dns.Msg{},
+			expected: []netip.Addr{},
+		},
+		"a_record": {
+			message: &dns.Msg{Answer: []dns.RR{
+				&dns.A{
+					Hdr: dns.RR_Header{Name: "example.com.", Rrtype: dns.TypeA, Class: dns.ClassINET},
+					A:   net.IP{1, 1, 1, 1},
+				},
+			}},
+			expected: []netip.Addr{netip.MustParseAddr("1.1.1.1")},
+		},
+		"aaaa_record": {
+			message: &dns.Msg{Answer: []dns.RR{
+				&dns.AAAA{
+					Hdr:  dns.RR_Header{Name: "example.com.", Rrtype: dns.TypeAAAA, Class: dns.ClassINET},
+					AAAA: net.IP{0x20, 0x01, 0x48, 0x60, 0x48, 0x60, 0, 0, 0, 0, 0, 0, 0, 0, 0x88, 0x88},
+				},
+			}},
+			expected: []netip.Addr{netip.MustParseAddr("2001:4860:4860::8888")},
+		},
+		"mixed_records": {
+			message: &dns.Msg{Answer: []dns.RR{
+				&dns.A{
+					Hdr: dns.RR_Header{Name: "example.com.", Rrtype: dns.TypeA, Class: dns.ClassINET},
+					A:   net.IP{1, 1, 1, 1},
+				},
+				&dns.AAAA{
+					Hdr:  dns.RR_Header{Name: "example.com.", Rrtype: dns.TypeAAAA, Class: dns.ClassINET},
+					AAAA: net.IP{0x20, 0x01, 0x48, 0x60, 0x48, 0x60, 0, 0, 0, 0, 0, 0, 0, 0, 0x88, 0x88},
+				},
+			}},
+			expected: []netip.Addr{netip.MustParseAddr("1.1.1.1"), netip.MustParseAddr("2001:4860:4860::8888")},
+		},
+	}
+
+	for testName, testCase := range testCases {
+		t.Run(testName, func(t *testing.T) {
+			t.Parallel()
+			addresses := answersToNetipAddrs(testCase.message)
+			assert.Equal(t, testCase.expected, addresses)
+		})
+	}
+}

internal/restrictednet/settings.go

@@ -0,0 +1,28 @@
+package restrictednet
+
+import (
+	"errors"
+
+	"github.com/qdm12/dns/v2/pkg/provider"
+)
+
+type Settings struct {
+	DefaultInterface  string
+	IPv6Supported     *bool
+	Firewall          Firewall
+	UpstreamResolvers []provider.Provider
+}
+
+func (s *Settings) validate() error {
+	switch {
+	case s.DefaultInterface == "":
+		return errors.New("default interface is not set")
+	case s.IPv6Supported == nil:
+		return errors.New("IPv6 support field is not set")
+	case s.Firewall == nil:
+		return errors.New("firewall is not set")
+	case len(s.UpstreamResolvers) == 0:
+		return errors.New("no upstream resolvers provided")
+	}
+	return nil
+}

internal/vpn/loop.go

@@ -45,6 +45,7 @@ type Loop struct {
 	start       <-chan struct{}
 	running     chan<- models.LoopStatus
 	userTrigger bool
+	healthDone  <-chan struct{}
 	// Internal constant values
 	backoffTime time.Duration
 }
@@ -70,6 +71,11 @@ func NewLoop(vpnSettings settings.VPN, ipv6SupportLevel netlink.IPv6SupportLevel
 	statusManager := loopstate.New(constants.Stopped, start, running, stop, stopped)
 	state := state.New(statusManager, vpnSettings)
 
+	// Initialize healthDone channel to a closed channel so that the first time
+	// we call <-l.healthDone it does not block
+	healthDone := make(chan struct{})
+	close(healthDone)
+
 	return &Loop{
 		statusManager:    statusManager,
 		state:            state,
@@ -98,6 +104,7 @@ func NewLoop(vpnSettings settings.VPN, ipv6SupportLevel netlink.IPv6SupportLevel
 		stop:             stop,
 		stopped:          stopped,
 		userTrigger:      true,
+		healthDone:       healthDone,
 		backoffTime:      defaultBackoffTime,
 	}
 }

internal/vpn/portforward.go

@@ -34,7 +34,9 @@ func (l *Loop) startPortForwarding(data tunnelUpData) (err error) {
 			Password:       data.password,
 		},
 	}
-	return l.portForward.UpdateWith(partialUpdate)
+	err = l.portForward.UpdateWith(partialUpdate)
+	l.logger.Debug(fmt.Sprintf("vpn loop: start port forwarding: error is %v", err))
+	return err
 }
 
 func (l *Loop) stopPortForwarding() (err error) {

internal/vpn/tunnelup.go

@@ -81,6 +81,7 @@ func (l *Loop) onTunnelUp(ctx, loopCtx context.Context, data tunnelUpData) {
 
 	_, _ = l.dnsLooper.ApplyStatus(ctx, constants.Running)
 
+	<-l.healthDone // make sure the health checker is stopped before restarting it
 	icmpTargetIPs := l.healthSettings.ICMPTargetIPs
 	if len(icmpTargetIPs) == 1 && icmpTargetIPs[0].IsUnspecified() {
 		icmpTargetIPs = []netip.Addr{data.serverIP}
@@ -104,7 +105,12 @@ func (l *Loop) onTunnelUp(ctx, loopCtx context.Context, data tunnelUpData) {
 	// Start collecting health errors asynchronously, since
 	// we should not wait for the code below to complete
 	// to start monitoring health and auto-healing.
-	go l.collectHealthErrors(ctx, loopCtx, healthErrCh)
+	// We keep track of when this goroutine is done with the healthDone
+	// channel to avoid a race condition where the health checker is stopped
+	// after being reconfigured and restarted, instead of before.
+	healthDone := make(chan struct{})
+	l.healthDone = healthDone
+	go l.collectHealthErrors(ctx, loopCtx, healthDone, healthErrCh)
 
 	err = l.publicip.RunOnce(ctx)
 	if err != nil {
@@ -140,7 +146,10 @@ func (l *Loop) onTunnelUp(ctx, loopCtx context.Context, data tunnelUpData) {
 	}
 }
 
-func (l *Loop) collectHealthErrors(ctx, loopCtx context.Context, healthErrCh <-chan error) {
+func (l *Loop) collectHealthErrors(ctx, loopCtx context.Context,
+	done chan<- struct{}, healthErrCh <-chan error,
+) {
+	defer close(done)
 	var previousHealthErr error
 	for {
 		select {