diff --git a/internal/platform/wayland/protocol_test.go b/internal/platform/wayland/protocol_test.go
index 53e7253..0c41f75 100644
--- a/internal/platform/wayland/protocol_test.go
+++ b/internal/platform/wayland/protocol_test.go
@@ -242,6 +242,11 @@ func TestNativeKeyboardBrowseSecureAndLearnTransitions(t *testing.T) {
 	monitor.key(t, 'h', 43, 0, false)
 	monitor.key(t, 'h', 43, 0, true)
 	await_command(t, keyboard, input.DocumentNextHeading)
+	if loadShiftPairs().unshifted['#'] == '3' {
+		monitor.key(t, '#', 12, 1, false)
+		monitor.key(t, '3', 12, 0, true)
+		await_command(t, keyboard, input.DocumentPreviousHeadingAtLevel3)
+	}
 	keyboard.SetNativeButtonFocus(true)
 	wait_snapshot(t, monitor, func(state MonitorSnapshot) bool {
 		for _, grab := range state.grabs {
diff --git a/internal/platform/wayland/routing.go b/internal/platform/wayland/routing.go
index 101488c..10b47d4 100644
--- a/internal/platform/wayland/routing.go
+++ b/internal/platform/wayland/routing.go
@@ -6,6 +6,7 @@ package wayland
 
 /*
 #cgo pkg-config: xkbcommon
+#include <stdlib.h>
 #include <xkbcommon/xkbcommon.h>
 */
 import "C"
@@ -14,6 +15,7 @@ import (
 	"errors"
 	"fmt"
 	"sort"
+	"sync"
 	"time"
 	"unsafe"
 
@@ -51,12 +53,101 @@ func key_name(symbol uint32) string {
 
 func lower_symbol(symbol uint32) uint32 { return uint32(C.xkb_keysym_to_lower(C.xkb_keysym_t(symbol))) }
 
-// KeyboardMonitor sends keysyms rather than a keymap. Letter case is defined
-// by XKB; punctuation's physical Shift pairing cannot be inferred from it.
+// KeyboardMonitor sends keysyms rather than a keymap, and the symbol for a
+// shifted key is the shifted keysym: Shift+3 arrives as numbersign on a US
+// layout. Letter case is defined by XKB alone, but a digit or punctuation
+// key's Shift partner depends on the layout. Bindings name the unshifted
+// symbol plus the Shift bit, as delivered by the Xorg path, so both grab
+// registration and event handling translate through shift pairs taken from
+// the default XKB keymap (the XKB_DEFAULT_* environment, else libxkbcommon
+// defaults). The monitor interface does not expose the compositor's keymap;
+// when its layout differs from that keymap, shifted digit and punctuation
+// chords keep the previous pass-through behavior instead of misfiring.
 func shifted_symbol(symbol uint32) uint32 {
 	return uint32(C.xkb_keysym_to_upper(C.xkb_keysym_t(symbol)))
 }
 
+type shiftPairs struct {
+	shifted   map[uint32][]uint32 // Unshifted symbol to its shifted partners.
+	unshifted map[uint32]uint32   // Shifted symbol to its one unshifted partner.
+}
+
+var loadShiftPairs = sync.OnceValue(func() shiftPairs { return build_shift_pairs("") })
+
+func shift_pair_base(symbol uint32) bool {
+	if symbol < '!' || symbol > '~' {
+		return false
+	}
+	return (symbol < 'A' || symbol > 'Z') && (symbol < 'a' || symbol > 'z')
+}
+
+func shift_pair_partner(symbol, base uint32) bool {
+	if symbol == 0 || symbol == base || symbol >= 0xfe00 {
+		return false // NoSymbol, unchanged, or dead/function/modifier ranges.
+	}
+	return (symbol < 'A' || symbol > 'Z') && (symbol < 'a' || symbol > 'z')
+}
+
+// An empty layout selects the default keymap; tests name layouts explicitly.
+func build_shift_pairs(layout string) shiftPairs {
+	pairs := shiftPairs{shifted: make(map[uint32][]uint32), unshifted: make(map[uint32]uint32)}
+	context := C.xkb_context_new(C.XKB_CONTEXT_NO_FLAGS)
+	if context == nil {
+		return pairs
+	}
+	C.xkb_context_set_log_level(context, C.XKB_LOG_LEVEL_CRITICAL) // Failure means empty pairs, not stderr noise.
+	defer C.xkb_context_unref(context)
+	var names C.struct_xkb_rule_names
+	if layout != "" {
+		clayout := C.CString(layout)
+		defer C.free(unsafe.Pointer(clayout))
+		names.layout = clayout
+	}
+	keymap := C.xkb_keymap_new_from_names(context, &names, C.XKB_KEYMAP_COMPILE_NO_FLAGS)
+	if keymap == nil {
+		return pairs
+	}
+	defer C.xkb_keymap_unref(keymap)
+	cshift := C.CString("Shift")
+	defer C.free(unsafe.Pointer(cshift))
+	shiftIndex := C.xkb_keymap_mod_get_index(keymap, cshift)
+	if shiftIndex == C.XKB_MOD_INVALID {
+		return pairs
+	}
+	state := C.xkb_state_new(keymap)
+	if state == nil {
+		return pairs
+	}
+	defer C.xkb_state_unref(state)
+	ambiguous := make(map[uint32]bool)
+	groups := C.xkb_keymap_num_layouts(keymap)
+	for group := C.xkb_layout_index_t(0); group < groups; group++ {
+		for code := C.xkb_keymap_min_keycode(keymap); code <= C.xkb_keymap_max_keycode(keymap); code++ {
+			C.xkb_state_update_mask(state, 0, 0, 0, 0, 0, group)
+			base := uint32(C.xkb_state_key_get_one_sym(state, code))
+			C.xkb_state_update_mask(state, 1<<shiftIndex, 0, 0, 0, 0, group)
+			shifted := uint32(C.xkb_state_key_get_one_sym(state, code))
+			if !shift_pair_base(base) || !shift_pair_partner(shifted, base) {
+				continue
+			}
+			found := false
+			for _, partner := range pairs.shifted[base] {
+				found = found || partner == shifted
+			}
+			if !found {
+				pairs.shifted[base] = append(pairs.shifted[base], shifted)
+			}
+			if previous, ok := pairs.unshifted[shifted]; ok && previous != base {
+				delete(pairs.unshifted, shifted)
+				ambiguous[shifted] = true
+			} else if !ambiguous[shifted] {
+				pairs.unshifted[shifted] = base
+			}
+		}
+	}
+	return pairs
+}
+
 func normalize_symbol(symbol uint32) uint32 {
 	symbol = lower_symbol(symbol)
 	if symbol == 0xfe20 {
@@ -91,6 +182,11 @@ func make_grabs(configuration keyboardConfiguration, policy keyboardPolicy) ([]u
 			if mask&3 != 0 {
 				unique[keyGrab{shifted_symbol(chord.Symbol), mask}] = true
 			}
+			if mask&1 != 0 {
+				for _, symbol := range loadShiftPairs().shifted[chord.Symbol] {
+					unique[keyGrab{symbol, mask}] = true
+				}
+			}
 		}
 	}
 	grabs := make([]keyGrab, 0, len(unique))
@@ -125,6 +221,13 @@ func (owner *keyboardOwner) handle_key(key keyEvent) error {
 	owner.sequence = max(owner.sequence+1, uint32(time.Since(owner.started).Milliseconds())+1)
 	timestamp := owner.sequence // One local clock shared by monitoring and commands.
 	symbol := normalize_symbol(key.symbol)
+	// Monitoring below keeps the raw symbol, so typing "#" still echoes as
+	// numbersign; only command lookup sees the unshifted binding symbol.
+	if key.state&1 != 0 {
+		if base, ok := loadShiftPairs().unshifted[symbol]; ok {
+			symbol = base
+		}
+	}
 	if key.symbol == 0xffb0 && owner.router.IsModifier(0xff9e) {
 		symbol = 0xff9e
 	}
diff --git a/internal/platform/wayland/routing_test.go b/internal/platform/wayland/routing_test.go
index b4a1728..496829d 100644
--- a/internal/platform/wayland/routing_test.go
+++ b/internal/platform/wayland/routing_test.go
@@ -136,6 +136,84 @@ func TestBrowseCaseLocksAndFocusedButton(t *testing.T) {
 	}
 }
 
+// Compositors emit the shifted keysym for Shift+digit (US layout: Shift+3 is
+// numbersign), while bindings name the unshifted digit plus the Shift bit.
+func TestShiftPairsFromKeymapLayouts(t *testing.T) {
+	us := build_shift_pairs("us")
+	for shifted, base := range map[uint32]uint32{'!': '1', '@': '2', '#': '3', '$': '4', '%': '5', '^': '6', ':': ';', '?': '/'} {
+		if us.unshifted[shifted] != base {
+			t.Fatalf("us shifted %q unshifts to %q, want %q", shifted, us.unshifted[shifted], base)
+		}
+	}
+	if partners := us.shifted['3']; len(partners) != 1 || partners[0] != '#' {
+		t.Fatalf("us partners for 3 = %v, want [#]", partners)
+	}
+	// The same physical chord differs by layout: GB Shift+3 is sterling.
+	gb := build_shift_pairs("gb")
+	if gb.unshifted[0xa3] != '3' {
+		t.Fatalf("gb sterling unshifts to %q, want 3", gb.unshifted[0xa3])
+	}
+	if empty := build_shift_pairs("no-such-layout"); len(empty.unshifted) != 0 || len(empty.shifted) != 0 {
+		t.Fatal("unknown layout produced shift pairs")
+	}
+}
+
+func TestBrowseShiftedDigitHeadingLevels(t *testing.T) {
+	if loadShiftPairs().unshifted['#'] != '3' {
+		t.Skip("default XKB keymap is not US-like; shifted symbols here assume US pairs")
+	}
+	configuration := keyboardConfiguration{layout: input.DesktopKeyboardLayout, modifiers: []string{"Insert"}}
+	previous := []input.Command{
+		input.DocumentPreviousHeadingAtLevel1, input.DocumentPreviousHeadingAtLevel2,
+		input.DocumentPreviousHeadingAtLevel3, input.DocumentPreviousHeadingAtLevel4,
+		input.DocumentPreviousHeadingAtLevel5, input.DocumentPreviousHeadingAtLevel6,
+	}
+	shifted := []uint32{'!', '@', '#', '$', '%', '^'}
+	for _, mask := range []uint32{0, 2, 16, 18} {
+		policy := keyboardPolicy{enabled: true, browse: true}
+		symbols, grabs, bindings := make_grabs(configuration, policy)
+		owner := test_owner(t, configuration.layout, "Insert")
+		owner.bindings, owner.policy, owner.router = bindings, policy, input.NewCommandRouter(symbols, bindings)
+		for level := 0; level < 6; level++ {
+			code := uint16(10 + level)
+			found := false
+			for _, grab := range grabs {
+				if grab == (keyGrab{shifted[level], mask | 1}) {
+					found = true
+				}
+			}
+			if !found {
+				t.Fatalf("shifted digit grab missing for level %d mask %d", level+1, mask)
+			}
+			send_key(t, owner, shifted[level], code, mask|1, false)
+			next_command(t, owner.keyboard, previous[level])
+			// Releasing Shift first changes the reported symbol to the digit.
+			send_key(t, owner, uint32('1'+level), code, mask, true)
+			if len(owner.held) != 0 {
+				t.Fatal("changed release symbol left a digit key held")
+			}
+			send_key(t, owner, uint32('1'+level), code, mask, false)
+			next_command(t, owner.keyboard, input.Command("document-next-heading-at-level-"+string(rune('1'+level))))
+			send_key(t, owner, uint32('1'+level), code, mask, true)
+		}
+	}
+	// Alt+Shift+digit heading lists share the translated symbol.
+	policy := keyboardPolicy{enabled: true, browse: true}
+	symbols, _, bindings := make_grabs(configuration, policy)
+	listOwner := test_owner(t, configuration.layout, "Insert")
+	listOwner.bindings, listOwner.policy, listOwner.router = bindings, policy, input.NewCommandRouter(symbols, bindings)
+	send_key(t, listOwner, '#', 12, 1|8, false)
+	next_command(t, listOwner.keyboard, input.DocumentListHeadingsAtLevel3)
+	send_key(t, listOwner, '3', 12, 8, true)
+	// Outside browse mode the shifted symbol must reach monitoring untouched.
+	owner := test_owner(t, input.DesktopKeyboardLayout, "Insert")
+	send_key(t, owner, '#', 12, 1, false)
+	event := <-owner.keyboard.events
+	if event.Name != "numbersign" || len(owner.keyboard.commands) != 0 {
+		t.Fatalf("plain typing changed to %q", event.Name)
+	}
+}
+
 func TestLearnModeAndSecureReset(t *testing.T) {
 	owner := test_owner(t, input.LaptopKeyboardLayout, "Insert")
 	send_key(t, owner, 0xff63, 118, 0, false)
@@ -149,6 +227,14 @@ func TestLearnModeAndSecureReset(t *testing.T) {
 	send_key(t, owner, 'q', 24, 0, false)
 	next_command(t, owner.keyboard, input.LearnKey)
 	send_key(t, owner, 'q', 24, 0, true)
+	if loadShiftPairs().unshifted['#'] == '3' {
+		send_key(t, owner, '#', 12, 1, false)
+		learned := next_command(t, owner.keyboard, input.LearnKey)
+		if learned.KeyName != "3" || learned.Chord.Symbol != '3' || learned.Chord.Modifiers != 1 {
+			t.Fatalf("learned shifted digit = %q %+v, want Shift+3", learned.KeyName, learned.Chord)
+		}
+		send_key(t, owner, '3', 12, 0, true)
+	}
 	send_key(t, owner, 0xff1b, 9, 0, false)
 	if next_command(t, owner.keyboard, input.ToggleLearnMode).LearnModeStarted {
 		t.Fatal("Escape restarted learn mode")