diff --git a/disco/disco.go b/disco/disco.go
index 0e7c3f7e5f882..8badad2dc895f 100644
--- a/disco/disco.go
+++ b/disco/disco.go
@@ -27,6 +27,7 @@ import (
 	"net/netip"
 
 	"go4.org/mem"
+	"golang.org/x/crypto/nacl/box"
 	"tailscale.com/types/key"
 )
 
@@ -48,6 +49,19 @@ const (
 
 const v0 = byte(0)
 
+// v1 Ping and Pong are padded as follows. CallMeMaybe is still on v0 and unpadded.
+const v1 = byte(1)
+
+// paddedPayloadLen is the desired length we want to pad Ping and Pong payloads
+// to so that they are the maximum size of a Wireguard packet we would
+// subsequently send. This ensures that any UDP paths we discover will actually
+// support the packet sizes the net stack will send over those paths. Any peers
+// behind a small-MTU link will have to depend on DERP.
+// c.f. https://github.com/coder/coder/issues/15523
+// Our inner IP packets can be up to 1280 bytes, with the Wireguard header of
+// 30 bytes, that is 1310. The final 2 is the inner payload header's type and version.
+const paddedPayloadLen = 1310 - len(Magic) - keyLen - NonceLen - box.Overhead - 2
+
 var errShort = errors.New("short message")
 
 // LooksLikeDiscoWrapper reports whether p looks like it's a packet
@@ -120,12 +134,8 @@ type Ping struct {
 }
 
 func (m *Ping) AppendMarshal(b []byte) []byte {
-	dataLen := 12
 	hasKey := !m.NodeKey.IsZero()
-	if hasKey {
-		dataLen += key.NodePublicRawLen
-	}
-	ret, d := appendMsgHeader(b, TypePing, v0, dataLen)
+	ret, d := appendMsgHeader(b, TypePing, v1, paddedPayloadLen)
 	n := copy(d, m.TxID[:])
 	if hasKey {
 		m.NodeKey.AppendTo(d[:n])
@@ -217,7 +227,7 @@ type Pong struct {
 const pongLen = 12 + 16 + 2
 
 func (m *Pong) AppendMarshal(b []byte) []byte {
-	ret, d := appendMsgHeader(b, TypePong, v0, pongLen)
+	ret, d := appendMsgHeader(b, TypePong, v1, paddedPayloadLen)
 	d = d[copy(d, m.TxID[:]):]
 	ip16 := m.Src.Addr().As16()
 	d = d[copy(d, ip16[:]):]
diff --git a/disco/disco_test.go b/disco/disco_test.go
index 67bd1561a9bf6..475203e0aa1d2 100644
--- a/disco/disco_test.go
+++ b/disco/disco_test.go
@@ -11,6 +11,7 @@ import (
 	"testing"
 
 	"go4.org/mem"
+	"golang.org/x/crypto/nacl/box"
 	"tailscale.com/types/key"
 )
 
@@ -25,7 +26,7 @@ func TestMarshalAndParse(t *testing.T) {
 			m: &Ping{
 				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
 			},
-			want: "01 00 01 02 03 04 05 06 07 08 09 0a 0b 0c",
+			want: "01 01 01 02 03 04 05 06 07 08 09 0a 0b 0c",
 		},
 		{
 			name: "ping_with_nodekey_src",
@@ -33,7 +34,7 @@ func TestMarshalAndParse(t *testing.T) {
 				TxID:    [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
 				NodeKey: key.NodePublicFromRaw32(mem.B([]byte{1: 1, 2: 2, 30: 30, 31: 31})),
 			},
-			want: "01 00 01 02 03 04 05 06 07 08 09 0a 0b 0c 00 01 02 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 1e 1f",
+			want: "01 01 01 02 03 04 05 06 07 08 09 0a 0b 0c 00 01 02 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 1e 1f",
 		},
 		{
 			name: "pong",
@@ -41,7 +42,7 @@ func TestMarshalAndParse(t *testing.T) {
 				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
 				Src:  mustIPPort("2.3.4.5:1234"),
 			},
-			want: "02 00 01 02 03 04 05 06 07 08 09 0a 0b 0c 00 00 00 00 00 00 00 00 00 00 ff ff 02 03 04 05 04 d2",
+			want: "02 01 01 02 03 04 05 06 07 08 09 0a 0b 0c 00 00 00 00 00 00 00 00 00 00 ff ff 02 03 04 05 04 d2",
 		},
 		{
 			name: "pongv6",
@@ -49,7 +50,7 @@ func TestMarshalAndParse(t *testing.T) {
 				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
 				Src:  mustIPPort("[fed0::12]:6666"),
 			},
-			want: "02 00 01 02 03 04 05 06 07 08 09 0a 0b 0c fe d0 00 00 00 00 00 00 00 00 00 00 00 00 00 12 1a 0a",
+			want: "02 01 01 02 03 04 05 06 07 08 09 0a 0b 0c fe d0 00 00 00 00 00 00 00 00 00 00 00 00 00 12 1a 0a",
 		},
 		{
 			name: "call_me_maybe",
@@ -75,10 +76,23 @@ func TestMarshalAndParse(t *testing.T) {
 			if !ok {
 				t.Fatalf("didn't start with foo: got %q", got)
 			}
+			// CODER: 1310 is max size of a Wireguard packet we will send.
+			expectedLen := 1310 - len(Magic) - keyLen - NonceLen - box.Overhead
+			switch tt.m.(type) {
+			case *Ping:
+				if len(got) != expectedLen {
+					t.Fatalf("Ping not padded: got len %d, want len %d", len(got), expectedLen)
+				}
+			case *Pong:
+				if len(got) != expectedLen {
+					t.Fatalf("Pong not padded: got len %d, want len %d", len(got), expectedLen)
+				}
+				// CallMeMaybe is unpadded
+			}
 
 			gotHex := fmt.Sprintf("% x", got)
-			if gotHex != tt.want {
-				t.Fatalf("wrong marshal\n got: %s\nwant: %s\n", gotHex, tt.want)
+			if !strings.HasPrefix(gotHex, tt.want) {
+				t.Fatalf("wrong marshal\n got: %s\nwant prefix: %s\n", gotHex, tt.want)
 			}
 
 			back, err := Parse([]byte(got))
@@ -92,6 +106,69 @@ func TestMarshalAndParse(t *testing.T) {
 	}
 }
 
+func TestParsePingPongV0(t *testing.T) {
+	tests := []struct {
+		name    string
+		payload []byte
+		m       Message
+	}{
+		{
+			name: "ping",
+			m: &Ping{
+				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
+			},
+			payload: []byte{0x01, 0x00, 0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c},
+		},
+		{
+			name: "ping_with_nodekey_src",
+			m: &Ping{
+				TxID:    [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
+				NodeKey: key.NodePublicFromRaw32(mem.B([]byte{1: 1, 2: 2, 30: 30, 31: 31})),
+			},
+			payload: []byte{
+				0x01, 0x00,
+				0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c,
+				0x00, 0x01, 0x02, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00,
+				0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x1e, 0x1f},
+		},
+		{
+			name: "pong",
+			m: &Pong{
+				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
+				Src:  mustIPPort("2.3.4.5:1234"),
+			},
+			payload: []byte{
+				0x02, 0x00,
+				0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c,
+				0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xff, 0xff, 0x02, 0x03, 0x04, 0x05,
+				0x04, 0xd2},
+		},
+		{
+			name: "pongv6",
+			m: &Pong{
+				TxID: [12]byte{1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12},
+				Src:  mustIPPort("[fed0::12]:6666"),
+			},
+			payload: []byte{
+				0x02, 0x00,
+				0x01, 0x02, 0x03, 0x04, 0x05, 0x06, 0x07, 0x08, 0x09, 0x0a, 0x0b, 0x0c,
+				0xfe, 0xd0, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x12,
+				0x1a, 0x0a},
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			back, err := Parse(tt.payload)
+			if err != nil {
+				t.Fatalf("parse back: %v", err)
+			}
+			if !reflect.DeepEqual(back, tt.m) {
+				t.Errorf("message in %+v doesn't match Parse result %+v", tt.m, back)
+			}
+		})
+	}
+}
+
 func mustIPPort(s string) netip.AddrPort {
 	ipp, err := netip.ParseAddrPort(s)
 	if err != nil {
diff --git a/wgengine/magicsock/magicsock.go b/wgengine/magicsock/magicsock.go
index 3c77a11353012..fc70b8ae6080c 100644
--- a/wgengine/magicsock/magicsock.go
+++ b/wgengine/magicsock/magicsock.go
@@ -2377,6 +2377,12 @@ func (c *Conn) bindSocket(ruc *RebindingUDPConn, network string, curPortFate cur
 			continue
 		}
 		trySetSocketBuffer(pconn, c.logf)
+		// CODER: https://github.com/coder/coder/issues/15523
+		// Attempt to tell the OS not to fragment packets over this interface. We pad disco Ping and Pong packets to the
+		// size of the direct UDP packets that get sent for direct connections. Thus, any interfaces or paths that
+		// cannot fully support direct connections due to MTU limitations will not be selected. If no direct paths meet
+		// the MTU requirements for a peer, we will fall back to DERP for that peer.
+		tryPreventFragmentation(pconn, c.logf, network)
 		// Success.
 		if debugBindSocket() {
 			c.logf("magicsock: bindSocket: successfully listened %v port %d", network, port)
diff --git a/wgengine/magicsock/magicsock_darwin.go b/wgengine/magicsock/magicsock_darwin.go
new file mode 100644
index 0000000000000..f3b32959f5ba8
--- /dev/null
+++ b/wgengine/magicsock/magicsock_darwin.go
@@ -0,0 +1,36 @@
+package magicsock
+
+import (
+	"net"
+
+	"golang.org/x/sys/unix"
+	"tailscale.com/types/logger"
+	"tailscale.com/types/nettype"
+)
+
+func tryPreventFragmentation(pconn nettype.PacketConn, logf logger.Logf, network string) {
+	if c, ok := pconn.(*net.UDPConn); ok {
+		s, err := c.SyscallConn()
+		if err != nil {
+			logf("magicsock: dontfrag: failed to get syscall conn: %v", err)
+		}
+		level := unix.IPPROTO_IP
+		option := unix.IP_DONTFRAG
+		if network == "udp6" {
+			level = unix.IPPROTO_IPV6
+			option = unix.IPV6_DONTFRAG
+		}
+		err = s.Control(func(fd uintptr) {
+			err := unix.SetsockoptInt(int(fd), level, option, 1)
+			if err != nil {
+				logf("magicsock: dontfrag: SetsockoptInt failed: %v", err)
+			}
+		})
+		if err != nil {
+			logf("magicsock: dontfrag: control connection failed: %v", err)
+		}
+		logf("magicsock: dontfrag: success on %s", pconn.LocalAddr().String())
+		return
+	}
+	logf("magicsock: dontfrag: failed because it was not a UDPConn")
+}
diff --git a/wgengine/magicsock/magicsock_linux.go b/wgengine/magicsock/magicsock_linux.go
index a4101ccbaa69d..f1be3d1cf40e0 100644
--- a/wgengine/magicsock/magicsock_linux.go
+++ b/wgengine/magicsock/magicsock_linux.go
@@ -404,3 +404,30 @@ func init() {
 	// message. These contain a single uint16 of data.
 	controlMessageSize = unix.CmsgSpace(2)
 }
+
+func tryPreventFragmentation(pconn nettype.PacketConn, logf logger.Logf, network string) {
+	if c, ok := pconn.(*net.UDPConn); ok {
+		s, err := c.SyscallConn()
+		if err != nil {
+			logf("magicsock: dontfrag: failed to get syscall conn: %v", err)
+		}
+		level := unix.IPPROTO_IP
+		option := unix.IP_MTU_DISCOVER
+		if network == "udp6" {
+			level = unix.IPPROTO_IPV6
+			option = unix.IPV6_MTU_DISCOVER
+		}
+		err = s.Control(func(fd uintptr) {
+			err := unix.SetsockoptInt(int(fd), level, option, unix.IP_PMTUDISC_DO)
+			if err != nil {
+				logf("magicsock: dontfrag: SetsockoptInt failed: %v", err)
+			}
+		})
+		if err != nil {
+			logf("magicsock: dontfrag: control connection failed: %v", err)
+		}
+		logf("magicsock: dontfrag: success on %s", pconn.LocalAddr().String())
+		return
+	}
+	logf("magicsock: dontfrag: failed because it was not a UDPConn")
+}
diff --git a/wgengine/magicsock/magicsock_windows.go b/wgengine/magicsock/magicsock_windows.go
new file mode 100644
index 0000000000000..0206fbc47c896
--- /dev/null
+++ b/wgengine/magicsock/magicsock_windows.go
@@ -0,0 +1,40 @@
+package magicsock
+
+import (
+	"net"
+
+	"golang.org/x/sys/windows"
+	"tailscale.com/types/logger"
+	"tailscale.com/types/nettype"
+)
+
+// https://github.com/tpn/winsdk-10/blob/9b69fd26ac0c7d0b83d378dba01080e93349c2ed/Include/10.0.16299.0/shared/ws2ipdef.h
+const (
+	IP_MTU_DISCOVER = 71 // IPV6_MTU_DISCOVER has the same value, which is nice.
+	IP_PMTUDISC_DO  = 1
+)
+
+func tryPreventFragmentation(pconn nettype.PacketConn, logf logger.Logf, network string) {
+	if c, ok := pconn.(*net.UDPConn); ok {
+		s, err := c.SyscallConn()
+		if err != nil {
+			logf("magicsock: dontfrag: failed to get syscall conn: %v", err)
+		}
+		level := windows.IPPROTO_IP
+		if network == "udp6" {
+			level = windows.IPPROTO_IPV6
+		}
+		err = s.Control(func(fd uintptr) {
+			err := windows.SetsockoptInt(windows.Handle(fd), level, IP_MTU_DISCOVER, IP_PMTUDISC_DO)
+			if err != nil {
+				logf("magicsock: dontfrag: SetsockoptInt failed: %v", err)
+			}
+		})
+		if err != nil {
+			logf("magicsock: dontfrag: control connection failed: %v", err)
+		}
+		logf("magicsock: dontfrag: success on %s", pconn.LocalAddr().String())
+		return
+	}
+	logf("magicsock: dontfrag: failed because it was not a UDPConn")
+}