diff --git a/pkg/connector/send_message.go b/pkg/connector/send_message.go
index fd54205..ef2dc55 100644
--- a/pkg/connector/send_message.go
+++ b/pkg/connector/send_message.go
@@ -747,6 +747,15 @@ func (lc *LineClient) HandleMatrixMessage(ctx context.Context, msg *bridgev2.Mat
 
 			if isGroup {
 				chunks, err = lc.E2EE.EncryptGroupMessageRaw(portalMid, fromMid, contentType, zipPayload)
+				if err != nil && !errors.Is(err, ltsm.ErrAbort) {
+					if errFetch := lc.fetchAndUnwrapGroupKey(ctx, portalMid, 0); errFetch == nil {
+						chunks, err = lc.E2EE.EncryptGroupMessageRaw(portalMid, fromMid, contentType, zipPayload)
+					} else if errors.Is(errFetch, ltsm.ErrAbort) {
+						return nil, errFetch
+					} else if errFetch = lineGroupE2EEFetchFailureError(errFetch); errFetch != nil {
+						return nil, errFetch
+					}
+				}
 			} else {
 				myRaw, myKeyID, errKey := lc.E2EE.MyKeyIDs()
 				if errKey != nil {
diff --git a/pkg/e2ee/manager.go b/pkg/e2ee/manager.go
index 42d62b6..b852743 100644
--- a/pkg/e2ee/manager.go
+++ b/pkg/e2ee/manager.go
@@ -49,8 +49,19 @@ type Manager struct {
 	groupSessionChannels map[string]map[int]map[int]int
 
 	latestGroupKey map[string]int // chatMid -> latest groupKeyId
+
+	groupKeyLRU        []groupKeyRef
+	groupNativeObjects int
+}
+
+type groupKeyRef struct {
+	chatMid    string
+	groupKeyID int
 }
 
+// LTSM's heap is a fixed 16 MiB, so the native objects kept for group chats are bounded.
+const maxGroupNativeObjects = 4096
+
 func NewManager() (*Manager, error) {
 	r, err := gen.GetRunner()
 	if err != nil {
@@ -473,8 +484,10 @@ func cipherVersion(chunks []string) (int, error) {
 func (m *Manager) UnwrapGroupSharedKey(chatMid string, sharedKey *line.E2EEGroupSharedKey) (int, error) {
 	m.mu.Lock()
 	defer m.mu.Unlock()
+	ref := groupKeyRef{chatMid, sharedKey.GroupKeyID}
 	if id := m.groupKeys[chatMid][sharedKey.GroupKeyID]; id != 0 {
 		m.latestGroupKey[chatMid] = sharedKey.GroupKeyID
+		m.touchGroupKeyLocked(ref)
 		return id, nil
 	}
 
@@ -512,8 +525,44 @@ func (m *Manager) UnwrapGroupSharedKey(chatMid string, sharedKey *line.E2EEGroup
 	m.groupKeys[chatMid][sharedKey.GroupKeyID] = unwrappedKeyID
 
 	m.latestGroupKey[chatMid] = sharedKey.GroupKeyID
+	m.groupNativeObjects++
+	m.touchGroupKeyLocked(ref)
+
+	return unwrappedKeyID, m.evictGroupKeysLocked()
+}
+
+func (m *Manager) touchGroupKeyLocked(ref groupKeyRef) {
+	for i := len(m.groupKeyLRU) - 1; i >= 0; i-- {
+		if m.groupKeyLRU[i] == ref {
+			m.groupKeyLRU = append(m.groupKeyLRU[:i], m.groupKeyLRU[i+1:]...)
+			break
+		}
+	}
+	m.groupKeyLRU = append(m.groupKeyLRU, ref)
+}
 
-	return unwrappedKeyID, nil
+func (m *Manager) evictGroupKeysLocked() error {
+	for m.groupNativeObjects > maxGroupNativeObjects && len(m.groupKeyLRU) > 1 {
+		ref := m.groupKeyLRU[0]
+		m.groupKeyLRU = m.groupKeyLRU[1:]
+		keyID := m.groupKeys[ref.chatMid][ref.groupKeyID]
+		m.groupNativeObjects -= 1 + len(m.groupSessionChannels[ref.chatMid][ref.groupKeyID])
+		delete(m.groupKeys[ref.chatMid], ref.groupKeyID)
+		if len(m.groupKeys[ref.chatMid]) == 0 {
+			delete(m.groupKeys, ref.chatMid)
+		}
+		delete(m.groupSessionChannels[ref.chatMid], ref.groupKeyID)
+		if len(m.groupSessionChannels[ref.chatMid]) == 0 {
+			delete(m.groupSessionChannels, ref.chatMid)
+		}
+		if m.latestGroupKey[ref.chatMid] == ref.groupKeyID {
+			delete(m.latestGroupKey, ref.chatMid)
+		}
+		if err := m.runner.KeyDestroy(keyID); err != nil && isFatalLTSMError(err) {
+			return err
+		}
+	}
+	return nil
 }
 
 // GenerateGroupKey generates a new Curve25519 key in the WASM module for use as a group key.
@@ -571,16 +620,12 @@ func (m *Manager) DecryptGroupMessage(msg *line.Message, chatMid string) (string
 	}
 
 	m.mu.Lock()
-	keyMap, ok := m.groupKeys[chatMid]
-	var unwrappedKeyID int
-	if ok {
-		unwrappedKeyID = keyMap[groupKeyID]
-	}
-	m.mu.Unlock()
-
+	defer m.mu.Unlock()
+	unwrappedKeyID := m.groupKeys[chatMid][groupKeyID]
 	if unwrappedKeyID == 0 {
 		return "", groupKeyID, fmt.Errorf("group key %d not found", groupKeyID)
 	}
+	m.touchGroupKeyLocked(groupKeyRef{chatMid, groupKeyID})
 
 	ver, err := cipherVersion(msg.Chunks)
 	if err != nil {
@@ -595,7 +640,7 @@ func (m *Manager) DecryptGroupMessage(msg *line.Message, chatMid string) (string
 	if err != nil {
 		return "", groupKeyID, err
 	}
-	chanID, err := m.ensureGroupChannel(chatMid, groupKeyID, unwrappedKeyID, senderKeyID)
+	chanID, err := m.ensureGroupChannelLocked(chatMid, groupKeyID, unwrappedKeyID, senderKeyID)
 	if err != nil {
 		return "", groupKeyID, err
 	}
@@ -628,10 +673,8 @@ func (m *Manager) DecryptGroupMessage(msg *line.Message, chatMid string) (string
 	return pt, groupKeyID, err
 }
 
-func (m *Manager) ensureGroupChannel(chatMid string, groupKeyID, unwrappedKeyID, senderKeyID int) (int, error) {
-	m.mu.Lock()
-	defer m.mu.Unlock()
-
+// Callers keep m.mu held while using the channel so an eviction cannot destroy it.
+func (m *Manager) ensureGroupChannelLocked(chatMid string, groupKeyID, unwrappedKeyID, senderKeyID int) (int, error) {
 	if m.groupSessionChannels[chatMid] == nil {
 		m.groupSessionChannels[chatMid] = make(map[int]map[int]int)
 	}
@@ -653,7 +696,8 @@ func (m *Manager) ensureGroupChannel(chatMid string, groupKeyID, unwrappedKeyID,
 	}
 
 	m.groupSessionChannels[chatMid][groupKeyID][senderKeyID] = chanID
-	return chanID, nil
+	m.groupNativeObjects++
+	return chanID, m.evictGroupKeysLocked()
 }
 
 func (m *Manager) EncryptGroupMessage(chatMid, fromMid string, plaintext string) ([]string, error) {
@@ -668,6 +712,7 @@ func (m *Manager) EncryptGroupMessage(chatMid, fromMid string, plaintext string)
 // Falls back to V1 if V2 fails (some clients like iOS still use V1).
 func (m *Manager) EncryptGroupMessageRaw(chatMid, fromMid string, contentType int, payload []byte) ([]string, error) {
 	m.mu.Lock()
+	defer m.mu.Unlock()
 	groupKeyID, ok := m.latestGroupKey[chatMid]
 	var unwrappedKeyID int
 	if ok {
@@ -676,13 +721,13 @@ func (m *Manager) EncryptGroupMessageRaw(chatMid, fromMid string, contentType in
 	myKeyID := m.myRawKeyID
 	seq := m.sequence[chatMid] + 1
 	m.sequence[chatMid] = seq
-	m.mu.Unlock()
 
 	if !ok || unwrappedKeyID == 0 {
 		return nil, fmt.Errorf("%w for group %s", ErrGroupKeyNotLoaded, chatMid)
 	}
+	m.touchGroupKeyLocked(groupKeyRef{chatMid, groupKeyID})
 
-	chanID, err := m.ensureGroupChannel(chatMid, groupKeyID, unwrappedKeyID, myKeyID)
+	chanID, err := m.ensureGroupChannelLocked(chatMid, groupKeyID, unwrappedKeyID, myKeyID)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/ltsm/runtime.go b/pkg/ltsm/runtime.go
index efbbc37..6894db0 100644
--- a/pkg/ltsm/runtime.go
+++ b/pkg/ltsm/runtime.go
@@ -335,6 +335,14 @@ func (rt *Runtime) E2EEKeyGetKeyId(keyPtr uint32) (int, error) {
 	return int(int32(result)), nil
 }
 
+func (rt *Runtime) E2EEKeyDestroy(ptr uint32) error {
+	return rt.imp.Destroy("E2EEKey", ptr)
+}
+
+func (rt *Runtime) E2EEChannelDestroy(ptr uint32) error {
+	return rt.imp.Destroy("E2EEChannel", ptr)
+}
+
 func (rt *Runtime) E2EEKeyGetPublicKey(keyPtr uint32) ([]byte, error) {
 	return rt.Curve25519KeyGetPublicKey(keyPtr)
 }
diff --git a/pkg/runner.go b/pkg/runner.go
index d806929..d50ad7e 100644
--- a/pkg/runner.go
+++ b/pkg/runner.go
@@ -190,6 +190,15 @@ func (r *Runner) unwrapGroupSharedKeyPanicSafe(chanPtr uint32, encKey []byte) (k
 	return r.rt.E2EEChannelUnwrapGroupSharedKey(chanPtr, encKey)
 }
 
+func (r *Runner) destroyPanicSafe(class string, destroy func(uint32) error, ptr uint32) (err error) {
+	defer func() {
+		if recovered := recover(); recovered != nil {
+			err = ltsmPanicError("ltsm "+class+" destroy", recovered)
+		}
+	}()
+	return destroy(ptr)
+}
+
 func (r *Runner) encryptV1PanicSafe(chanPtr uint32, plaintext []byte) (ciphertext []byte, err error) {
 	defer func() {
 		if recovered := recover(); recovered != nil {
@@ -664,6 +673,32 @@ func (r *Runner) ChannelUnwrapGroupSharedKey(channelID int, encryptedSharedKeyB6
 	return r.putKey(keyPtr), nil
 }
 
+// KeyDestroy releases an unwrapped group key and every channel created from it.
+func (r *Runner) KeyDestroy(keyID int) error {
+	r.mu.Lock()
+	defer r.mu.Unlock()
+
+	keyPtr, err := r.getKey(keyID)
+	if err != nil {
+		return err
+	}
+	var errs []error
+	for cacheKey, channelID := range r.channelsByKey {
+		if cacheKey.keyID != keyID {
+			continue
+		}
+		chanPtr := r.channelStore[channelID]
+		delete(r.channelsByKey, cacheKey)
+		delete(r.channelStore, channelID)
+		delete(r.goChannels, channelID)
+		errs = append(errs, r.destroyPanicSafe("E2EEChannel", r.rt.E2EEChannelDestroy, chanPtr))
+	}
+	delete(r.keyStore, keyID)
+	delete(r.goKeys, keyID)
+	errs = append(errs, r.destroyPanicSafe("E2EEKey", r.rt.E2EEKeyDestroy, keyPtr))
+	return errors.Join(errs...)
+}
+
 // ChannelEncryptV1 encrypts plaintext with channel V1 (AES-256-CBC + MAC).
 // Uses pure Go crypto when a Go channel is available.
 func (r *Runner) ChannelEncryptV1(channelID int, plaintext string) (string, error) {