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tstest/integration/vms: smoke test derphttp through mitm proxies

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Updates #4377

Very smoky/high-level test to ensure that derphttp internals play well
with an agressive (stare + bump) meddler-in-the-middle proxy.

Signed-off-by: Tom DNetto <tom@tailscale.com>
This commit is contained in:
Tom DNetto 2022-04-12 13:04:36 -07:00 committed by Tom
parent 2748750aa2
commit dec68166e4
5 changed files with 175 additions and 20 deletions
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2
tstest/integration/vms/nixos_test.go
View File

@ -124,7 +124,7 @@
systemd.services.cloud-final.path = with pkgs; [ curl ];
# Curl is needed for one of the integration tests
environment.systemPackages = with pkgs; [ curl ];
environment.systemPackages = with pkgs; [ curl nix bash squid openssl daemonize ];
# yolo, this vm can sudo freely.
security.sudo.wheelNeedsPassword = false;

39
tstest/integration/vms/squid.conf Normal file
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@ -0,0 +1,39 @@
pid_filename /run/squid.pid
cache_dir ufs /tmp/squid/cache 500 16 256
maximum_object_size 4096 KB
coredump_dir /tmp/squid/core
visible_hostname localhost
cache_access_log /tmp/squid/access.log
cache_log /tmp/squid/cache.log
# Access Control lists
acl localhost src 127.0.0.1 ::1
acl manager proto cache_object
acl SSL_ports port 443
acl Safe_ports port 80 # http
acl Safe_ports port 21 # ftp
acl Safe_ports port 443 # https
acl Safe_ports port 70 # gopher
acl Safe_ports port 210 # wais
acl Safe_ports port 1025-65535 # unregistered ports
acl Safe_ports port 280 # http-mgmt
acl Safe_ports port 488 # gss-http
acl Safe_ports port 591 # filemaker
acl Safe_ports port 777 # multiling http
acl CONNECT method CONNECT
http_access allow localhost
http_access deny all
forwarded_for on
# sslcrtd_program /nix/store/nqlqk1f6qlxdirlrl1aijgb6vbzxs0gs-squid-4.17/libexec/security_file_certgen -s /tmp/squid/ssl_db -M 4MB
sslcrtd_children 5
http_port 127.0.0.1:3128 \
ssl-bump \
generate-host-certificates=on \
dynamic_cert_mem_cache_size=4MB \
cert=/tmp/squid/myca-mitm.pem
ssl_bump stare all # mimic the Client Hello, drop unsupported extensions
ssl_bump bump all # terminate and establish new TLS connection

110
tstest/integration/vms/top_level_test.go
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@ -7,20 +7,120 @@
package vms
import "testing"
import (
"context"
"testing"
"time"
"github.com/pkg/sftp"
expect "github.com/tailscale/goexpect"
)
func TestRunUbuntu1804(t *testing.T) {
setupTests(t)
testOneDistribution(t, 0, Distros[0])
}
func TestRunUbuntu2004(t *testing.T) {
setupTests(t)
testOneDistribution(t, 1, Distros[1])
}
func TestRunNixos2111(t *testing.T) {
t.Parallel()
setupTests(t)
testOneDistribution(t, 2, Distros[2])
}
}
// TestMITMProxy is a smoke test for derphttp through a MITM proxy.
// Encountering such proxies is unfortunately commonplace in more
// traditional enterprise networks.
//
// We invoke tailscale netcheck because the networking check is done
// by tailscale rather than tailscaled, making it easier to configure
// the proxy.
//
// To provide the actual MITM server, we use squid.
func TestMITMProxy(t *testing.T) {
t.Parallel()
setupTests(t)
distro := Distros[2] // nixos-21.11
if distroRex.Unwrap().MatchString(distro.Name) {
t.Logf("%s matches %s", distro.Name, distroRex.Unwrap())
} else {
t.Skip("regex not matched")
}
ctx, done := context.WithCancel(context.Background())
t.Cleanup(done)
h := newHarness(t)
err := ramsem.sem.Acquire(ctx, int64(distro.MemoryMegs))
if err != nil {
t.Fatalf("can't acquire ram semaphore: %v", err)
}
t.Cleanup(func() { ramsem.sem.Release(int64(distro.MemoryMegs)) })
vm := h.mkVM(t, 2, distro, h.pubKey, h.loginServerURL, t.TempDir())
vm.waitStartup(t)
ipm := h.waitForIPMap(t, vm, distro)
_, cli := h.setupSSHShell(t, distro, ipm)
sftpCli, err := sftp.NewClient(cli)
if err != nil {
t.Fatalf("can't connect over sftp to copy binaries: %v", err)
}
defer sftpCli.Close()
// Initialize a squid installation.
//
// A few things of note here:
// - The first thing we do is append the nsslcrtd_program stanza to the config.
// This must be an absolute path and is based on the nix path of the squid derivation,
// so we compute and write it out here.
// - Squid expects a pre-initalized directory layout, so we create that in /tmp/squid then
// invoke squid with -z to have it fill in the rest.
// - Doing a meddler-in-the-middle attack requires using some fake keys, so we create
// them using openssl and then use the security_file_certgen tool to setup squids' ssl_db.
// - There were some perms issues, so i yeeted 0777. Its only a test anyway
copyFile(t, sftpCli, "squid.conf", "/tmp/squid.conf")
runTestCommands(t, 30*time.Second, cli, []expect.Batcher{
&expect.BSnd{S: "echo -e \"\\nsslcrtd_program $(nix eval --raw nixpkgs.squid)/libexec/security_file_certgen -s /tmp/squid/ssl_db -M 4MB\\n\" >> /tmp/squid.conf\n"},
&expect.BSnd{S: "mkdir -p /tmp/squid/{cache,core}\n"},
&expect.BSnd{S: "openssl req -batch -new -newkey rsa:4096 -sha256 -days 3650 -nodes -x509 -keyout /tmp/squid/myca-mitm.pem -out /tmp/squid/myca-mitm.pem\n"},
&expect.BExp{R: `writing new private key to '/tmp/squid/myca-mitm.pem'`},
&expect.BSnd{S: "$(nix eval --raw nixpkgs.squid)/libexec/security_file_certgen -c -s /tmp/squid/ssl_db -M 4MB\n"},
&expect.BExp{R: `Done`},
&expect.BSnd{S: "sudo chmod -R 0777 /tmp/squid\n"},
&expect.BSnd{S: "squid --foreground -YCs -z -f /tmp/squid.conf\n"},
&expect.BSnd{S: "echo Success.\n"},
&expect.BExp{R: `Success.`},
})
// Start the squid server.
runTestCommands(t, 10*time.Second, cli, []expect.Batcher{
&expect.BSnd{S: "daemonize -v -c /tmp/squid $(nix eval --raw nixpkgs.squid)/bin/squid --foreground -YCs -f /tmp/squid.conf\n"}, // start daemon
// NOTE(tom): Writing to /dev/tcp/* is bash magic, not a file. This
// eldritchian incantation lets us wait till squid is up.
&expect.BSnd{S: "while ! timeout 5 bash -c 'echo > /dev/tcp/localhost/3128'; do sleep 1; done\n"},
&expect.BSnd{S: "echo Success.\n"},
&expect.BExp{R: `Success.`},
})
// Uncomment to help debugging this test if it fails.
//
// runTestCommands(t, 30 * time.Second, cli, []expect.Batcher{
// &expect.BSnd{S: "sudo ifconfig\n"},
// &expect.BSnd{S: "sudo ip link\n"},
// &expect.BSnd{S: "sudo ip route\n"},
// &expect.BSnd{S: "ps -aux\n"},
// &expect.BSnd{S: "netstat -a\n"},
// &expect.BSnd{S: "cat /tmp/squid/access.log && cat /tmp/squid/cache.log && cat /tmp/squid.conf && echo Success.\n"},
// &expect.BExp{R: `Success.`},
// })
runTestCommands(t, 30*time.Second, cli, []expect.Batcher{
&expect.BSnd{S: "SSL_CERT_FILE=/tmp/squid/myca-mitm.pem HTTPS_PROXY=http://127.0.0.1:3128 tailscale netcheck\n"},
&expect.BExp{R: `IPv4: yes`},
})
}

14
tstest/integration/vms/vm_setup_test.go
View File

@ -23,6 +23,7 @@
"strconv"
"strings"
"testing"
"time"
"github.com/aws/aws-sdk-go-v2/aws"
"github.com/aws/aws-sdk-go-v2/config"
@ -49,6 +50,19 @@ func (vm *vmInstance) running() bool {
}
}
func (vm *vmInstance) waitStartup(t *testing.T) {
t.Helper()
for i := 0; i < 100; i++ {
if vm.running() {
break
}
time.Sleep(100 * time.Millisecond)
}
if !vm.running() {
t.Fatal("vm not running")
}
}
func (h *Harness) makeImage(t *testing.T, d Distro, cdir string) string {
if !strings.HasPrefix(d.Name, "nixos") {
t.Fatal("image generation for non-nixos is not implemented")

30
tstest/integration/vms/vms_test.go
View File

@ -276,17 +276,14 @@ func testOneDistribution(t *testing.T, n int, distro Distro) {
t.Cleanup(func() { ramsem.sem.Release(int64(distro.MemoryMegs)) })
vm := h.mkVM(t, n, distro, h.pubKey, h.loginServerURL, dir)
var ipm ipMapping
vm.waitStartup(t)
for i := 0; i < 100; i++ {
if vm.running() {
break
}
time.Sleep(100 * time.Millisecond)
}
if !vm.running() {
t.Fatal("vm not running")
}
h.testDistro(t, distro, h.waitForIPMap(t, vm, distro))
}
func (h *Harness) waitForIPMap(t *testing.T, vm *vmInstance, distro Distro) ipMapping {
t.Helper()
var ipm ipMapping
waiter := time.NewTicker(time.Second)
defer waiter.Stop()
@ -305,13 +302,11 @@ func testOneDistribution(t *testing.T, n int, distro Distro) {
}
<-waiter.C
}
h.testDistro(t, distro, ipm)
return ipm
}
func (h *Harness) testDistro(t *testing.T, d Distro, ipm ipMapping) {
func (h *Harness) setupSSHShell(t *testing.T, d Distro, ipm ipMapping) (*ssh.ClientConfig, *ssh.Client) {
signer := h.signer
loginServer := h.loginServerURL
t.Helper()
port := ipm.port
@ -350,6 +345,13 @@ func (h *Harness) testDistro(t *testing.T, d Distro, ipm ipMapping) {
}
h.copyBinaries(t, d, cli)
return ccfg, cli
}
func (h *Harness) testDistro(t *testing.T, d Distro, ipm ipMapping) {
loginServer := h.loginServerURL
ccfg, cli := h.setupSSHShell(t, d, ipm)
timeout := 30 * time.Second
t.Run("start-tailscale", func(t *testing.T) {