diff --git a/ssh/tailssh/incubator.go b/ssh/tailssh/incubator.go
index e0ab34d0d..17ecd6a14 100644
--- a/ssh/tailssh/incubator.go
+++ b/ssh/tailssh/incubator.go
@@ -235,6 +235,7 @@ func beIncubator(args []string) error {
 	if err == nil && sessionCloser != nil {
 		defer sessionCloser()
 	}
+
 	var groupIDs []int
 	for _, g := range strings.Split(ia.groups, ",") {
 		gid, err := strconv.ParseInt(g, 10, 32)
@@ -244,22 +245,10 @@ func beIncubator(args []string) error {
 		groupIDs = append(groupIDs, int(gid))
 	}
 
-	if err := setGroups(groupIDs); err != nil {
+	if err := dropPrivileges(logf, int(ia.uid), ia.gid, groupIDs); err != nil {
 		return err
 	}
-	if egid := os.Getegid(); egid != ia.gid {
-		if err := syscall.Setgid(int(ia.gid)); err != nil {
-			logf(err.Error())
-			os.Exit(1)
-		}
-	}
-	if euid != ia.uid {
-		// Switch users if required before starting the desired process.
-		if err := syscall.Setuid(int(ia.uid)); err != nil {
-			logf(err.Error())
-			os.Exit(1)
-		}
-	}
+
 	if ia.isSFTP {
 		logf("handling sftp")
 
@@ -304,6 +293,108 @@ func beIncubator(args []string) error {
 	return err
 }
 
+// TODO(andrew-d): verify that this works in more configurations before
+// enabling by default.
+const assertDropPrivileges = false
+
+// dropPrivileges contains all the logic for dropping privileges to a different
+// UID, GID, and set of supplementary groups. This function is
+// security-sensitive and ordering-dependent; please be very cautious if/when
+// refactoring.
+//
+// WARNING: if you change this function, you *MUST* run the TestDropPrivileges
+// test in this package as root on at least Linux, FreeBSD and Darwin. This can
+// be done by running:
+//
+//	go test -c ./ssh/tailssh/ && sudo ./tailssh.test -test.v -test.run TestDropPrivileges
+func dropPrivileges(logf logger.Logf, wantUid, wantGid int, supplementaryGroups []int) error {
+	fatalf := func(format string, args ...any) {
+		logf(format, args...)
+		os.Exit(1)
+	}
+
+	euid := os.Geteuid()
+	egid := os.Getegid()
+
+	if runtime.GOOS == "darwin" || runtime.GOOS == "freebsd" {
+		// On FreeBSD and Darwin, the first entry returned from the
+		// getgroups(2) syscall is the egid, and changing it with
+		// setgroups(2) changes the egid of the process. This is
+		// technically a violation of the POSIX standard; see the
+		// following article for more detail:
+		//    https://www.usenix.org/system/files/login/articles/325-tsafrir.pdf
+		//
+		// In this case, we add an entry at the beginning of the
+		// groupIDs list containing the expected gid if it's not
+		// already there, which modifies the egid and additional groups
+		// as one unit.
+		if len(supplementaryGroups) == 0 || supplementaryGroups[0] != wantGid {
+			supplementaryGroups = append([]int{wantGid}, supplementaryGroups...)
+		}
+	}
+
+	if err := setGroups(supplementaryGroups); err != nil {
+		return err
+	}
+	if egid != wantGid {
+		// On FreeBSD and Darwin, we may have already called the
+		// equivalent of setegid(wantGid) via the call to setGroups,
+		// above. However, per the manpage, setgid(getegid()) is an
+		// allowed operation regardless of privilege level.
+		//
+		// FreeBSD:
+		//	The setgid() system call is permitted if the specified ID
+		//	is equal to the real group ID or the effective group ID
+		//	of the process, or if the effective user ID is that of
+		//	the super user.
+		//
+		// Darwin:
+		//	The setgid() function is permitted if the effective
+		//	user ID is that of the super user, or if the specified
+		//	group ID is the same as the effective group ID.  If
+		//	not, but the specified group ID is the same as the real
+		//	group ID, setgid() will set the effective group ID to
+		//	the real group ID.
+		if err := syscall.Setgid(wantGid); err != nil {
+			fatalf("Setgid(%d): %v", wantGid, err)
+		}
+	}
+	if euid != wantUid {
+		// Switch users if required before starting the desired process.
+		if err := syscall.Setuid(wantUid); err != nil {
+			fatalf("Setuid(%d): %v", wantUid, err)
+		}
+	}
+
+	// If we changed either the UID or GID, defensively assert that we
+	// cannot reset the it back to our original values, and that the
+	// current egid/euid are the expected values after we change
+	// everything; if not, we exit the process.
+	if assertDropPrivileges {
+		if egid != wantGid {
+			if err := syscall.Setegid(egid); err == nil {
+				fatalf("unexpectedly able to set egid back to %d", egid)
+			}
+		}
+		if euid != wantUid {
+			if err := syscall.Seteuid(euid); err == nil {
+				fatalf("unexpectedly able to set euid back to %d", euid)
+			}
+		}
+
+		if got := os.Getegid(); got != wantGid {
+			fatalf("got egid=%d, want %d", got, wantGid)
+		}
+		if got := os.Geteuid(); got != wantUid {
+			fatalf("got euid=%d, want %d", got, wantUid)
+		}
+
+		// TODO(andrew-d): assert that our supplementary groups are correct
+	}
+
+	return nil
+}
+
 // launchProcess launches an incubator process for the provided session.
 // It is responsible for configuring the process execution environment.
 // The caller can wait for the process to exit by calling cmd.Wait().
diff --git a/ssh/tailssh/privs_test.go b/ssh/tailssh/privs_test.go
new file mode 100644
index 000000000..60cfe5e4f
--- /dev/null
+++ b/ssh/tailssh/privs_test.go
@@ -0,0 +1,295 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+
+//go:build linux || darwin || freebsd || openbsd || netbsd || dragonfly
+
+package tailssh
+
+import (
+	"encoding/json"
+	"errors"
+	"os"
+	"os/exec"
+	"os/user"
+	"path/filepath"
+	"reflect"
+	"regexp"
+	"runtime"
+	"strconv"
+	"syscall"
+	"testing"
+
+	"golang.org/x/exp/slices"
+	"tailscale.com/types/logger"
+)
+
+func TestDropPrivileges(t *testing.T) {
+	type SubprocInput struct {
+		UID              int
+		GID              int
+		AdditionalGroups []int
+	}
+	type SubprocOutput struct {
+		UID              int
+		GID              int
+		EUID             int
+		EGID             int
+		AdditionalGroups []int
+	}
+
+	if v := os.Getenv("TS_TEST_DROP_PRIVILEGES_CHILD"); v != "" {
+		t.Logf("in child process")
+
+		var input SubprocInput
+		if err := json.Unmarshal([]byte(v), &input); err != nil {
+			t.Fatal(err)
+		}
+
+		// Get a handle to our provided JSON file before dropping privs.
+		f := os.NewFile(3, "out.json")
+
+		// We're in our subprocess; actually drop privileges now.
+		dropPrivileges(t.Logf, input.UID, input.GID, input.AdditionalGroups)
+
+		additional, _ := syscall.Getgroups()
+
+		// Print our IDs
+		json.NewEncoder(f).Encode(SubprocOutput{
+			UID:              os.Getuid(),
+			GID:              os.Getgid(),
+			EUID:             os.Geteuid(),
+			EGID:             os.Getegid(),
+			AdditionalGroups: additional,
+		})
+
+		// Close output file to ensure that it's flushed to disk before we exit
+		f.Close()
+
+		// Always exit the process now that we have a different
+		// UID/GID/etc.; we don't want the Go test framework to try and
+		// clean anything up, since it might no longer have access.
+		os.Exit(0)
+	}
+
+	if os.Getuid() != 0 {
+		t.Skip("test only works when run as root")
+	}
+
+	rerunSelf := func(t *testing.T, input SubprocInput) []byte {
+		fpath := filepath.Join(t.TempDir(), "out.json")
+		outf, err := os.Create(fpath)
+		if err != nil {
+			t.Fatal(err)
+		}
+
+		inputb, err := json.Marshal(input)
+		if err != nil {
+			t.Fatal(err)
+		}
+
+		cmd := exec.Command(os.Args[0], "-test.v", "-test.run", "^"+regexp.QuoteMeta(t.Name())+"$")
+		cmd.Env = append(os.Environ(), "TS_TEST_DROP_PRIVILEGES_CHILD="+string(inputb))
+		cmd.ExtraFiles = []*os.File{outf}
+		cmd.Stdout = logger.FuncWriter(logger.WithPrefix(t.Logf, "child: "))
+		cmd.Stderr = logger.FuncWriter(logger.WithPrefix(t.Logf, "child: "))
+		if err := cmd.Run(); err != nil {
+			t.Fatal(err)
+		}
+		outf.Close()
+
+		jj, err := os.ReadFile(fpath)
+		if err != nil {
+			t.Fatal(err)
+		}
+		return jj
+	}
+
+	// We want to ensure we're not colliding with existing users; find some
+	// unused UIDs and GIDs for the tests we run.
+	uid1 := findUnusedUID(t)
+	gid1 := findUnusedGID(t)
+	gid2 := findUnusedGID(t, gid1)
+	gid3 := findUnusedGID(t, gid1, gid2)
+
+	// For some tests, we want a UID/GID pair with the same numerical
+	// value; this finds one.
+	uidgid1 := findUnusedUIDGID(t, uid1, gid1, gid2, gid3)
+
+	t.Logf("uid1=%d gid1=%d gid2=%d gid3=%d uidgid1=%d",
+		uid1, gid1, gid2, gid3, uidgid1)
+
+	testCases := []struct {
+		name             string
+		uid              int
+		gid              int
+		additionalGroups []int
+	}{
+		{
+			name:             "all_different_values",
+			uid:              uid1,
+			gid:              gid1,
+			additionalGroups: []int{gid2, gid3},
+		},
+		{
+			name:             "no_additional_groups",
+			uid:              uid1,
+			gid:              gid1,
+			additionalGroups: []int{},
+		},
+		// This is a regression test for the following bug, triggered
+		// on Darwin & FreeBSD:
+		//    https://github.com/tailscale/tailscale/issues/7616
+		{
+			name:             "same_values",
+			uid:              uidgid1,
+			gid:              uidgid1,
+			additionalGroups: []int{uidgid1},
+		},
+	}
+
+	for _, tt := range testCases {
+		t.Run(tt.name, func(t *testing.T) {
+			subprocOut := rerunSelf(t, SubprocInput{
+				UID:              tt.uid,
+				GID:              tt.gid,
+				AdditionalGroups: tt.additionalGroups,
+			})
+
+			var out SubprocOutput
+			if err := json.Unmarshal(subprocOut, &out); err != nil {
+				t.Logf("%s", subprocOut)
+				t.Fatal(err)
+			}
+			t.Logf("output: %+v", out)
+
+			if out.UID != tt.uid {
+				t.Errorf("got uid %d; want %d", out.UID, tt.uid)
+			}
+			if out.GID != tt.gid {
+				t.Errorf("got gid %d; want %d", out.GID, tt.gid)
+			}
+			if out.EUID != tt.uid {
+				t.Errorf("got euid %d; want %d", out.EUID, tt.uid)
+			}
+			if out.EGID != tt.gid {
+				t.Errorf("got egid %d; want %d", out.EGID, tt.gid)
+			}
+
+			// On FreeBSD and Darwin, the set of additional groups
+			// is prefixed with the egid; handle that case by
+			// modifying our expected set.
+			wantGroups := make(map[int]bool)
+			for _, id := range tt.additionalGroups {
+				wantGroups[id] = true
+			}
+			if runtime.GOOS == "darwin" || runtime.GOOS == "freebsd" {
+				wantGroups[tt.gid] = true
+			}
+
+			gotGroups := make(map[int]bool)
+			for _, id := range out.AdditionalGroups {
+				gotGroups[id] = true
+			}
+
+			if !reflect.DeepEqual(gotGroups, wantGroups) {
+				t.Errorf("got additional groups %+v; want %+v", gotGroups, wantGroups)
+			}
+		})
+	}
+}
+
+func findUnusedUID(t *testing.T, not ...int) int {
+	for i := 1000; i < 65535; i++ {
+		// Skip UIDs that might be valid
+		if maybeValidUID(i) {
+			continue
+		}
+
+		// Skip UIDs that we're avoiding
+		if slices.Contains(not, i) {
+			continue
+		}
+
+		// Not a valid UID, not one we're avoiding... all good!
+		return i
+	}
+
+	t.Fatalf("unable to find an unused UID")
+	return -1
+}
+
+func findUnusedGID(t *testing.T, not ...int) int {
+	for i := 1000; i < 65535; i++ {
+		if maybeValidGID(i) {
+			continue
+		}
+
+		// Skip GIDs that we're avoiding
+		if slices.Contains(not, i) {
+			continue
+		}
+
+		// Not a valid GID, not one we're avoiding... all good!
+		return i
+	}
+
+	t.Fatalf("unable to find an unused GID")
+	return -1
+}
+
+func findUnusedUIDGID(t *testing.T, not ...int) int {
+	for i := 1000; i < 65535; i++ {
+		if maybeValidUID(i) || maybeValidGID(i) {
+			continue
+		}
+
+		// Skip IDs that we're avoiding
+		if slices.Contains(not, i) {
+			continue
+		}
+
+		// Not a valid ID, not one we're avoiding... all good!
+		return i
+	}
+
+	t.Fatalf("unable to find an unused UID/GID pair")
+	return -1
+}
+
+func maybeValidUID(id int) bool {
+	_, err := user.LookupId(strconv.Itoa(id))
+	if err == nil {
+		return true
+	}
+
+	var u1 user.UnknownUserIdError
+	if errors.As(err, &u1) {
+		return false
+	}
+	var u2 user.UnknownUserError
+	if errors.As(err, &u2) {
+		return false
+	}
+
+	// Some other error; might be valid
+	return true
+}
+
+func maybeValidGID(id int) bool {
+	_, err := user.LookupGroupId(strconv.Itoa(id))
+	if err == nil {
+		return true
+	}
+
+	var u1 user.UnknownGroupIdError
+	if errors.As(err, &u1) {
+		return false
+	}
+	var u2 user.UnknownGroupError
+	if errors.As(err, &u2) {
+		return false
+	}
+
+	// Some other error; might be valid
+	return true
+}