diff --git a/internal/provider/gemini-web/state.go b/internal/provider/gemini-web/state.go
index cd6c5af5..e9ee8f13 100644
--- a/internal/provider/gemini-web/state.go
+++ b/internal/provider/gemini-web/state.go
@@ -56,6 +56,12 @@ type GeminiWebState struct {
 	pendingMatch   *conversation.MatchResult
 }
 
+type reuseComputation struct {
+	metadata []string
+	history  []RoleText
+	overlap  int
+}
+
 func NewGeminiWebState(cfg *config.Config, token *gemini.GeminiWebTokenStorage, storagePath, authLabel string) *GeminiWebState {
 	state := &GeminiWebState{
 		cfg:         cfg,
@@ -155,6 +161,78 @@ func (s *GeminiWebState) convPath() string {
 	return ConvBoltPath(base)
 }
 
+func cloneRoleTextSlice(in []RoleText) []RoleText {
+	if len(in) == 0 {
+		return nil
+	}
+	out := make([]RoleText, len(in))
+	copy(out, in)
+	return out
+}
+
+func cloneStringSlice(in []string) []string {
+	if len(in) == 0 {
+		return nil
+	}
+	out := make([]string, len(in))
+	copy(out, in)
+	return out
+}
+
+func longestHistoryOverlap(history, incoming []RoleText) int {
+	max := len(history)
+	if len(incoming) < max {
+		max = len(incoming)
+	}
+	for overlap := max; overlap > 0; overlap-- {
+		if conversation.EqualMessages(history[len(history)-overlap:], incoming[:overlap]) {
+			return overlap
+		}
+	}
+	return 0
+}
+
+func equalStringSlice(a, b []string) bool {
+	if len(a) != len(b) {
+		return false
+	}
+	for i := range a {
+		if a[i] != b[i] {
+			return false
+		}
+	}
+	return true
+}
+
+func storedMessagesToRoleText(stored []conversation.StoredMessage) []RoleText {
+	if len(stored) == 0 {
+		return nil
+	}
+	converted := make([]RoleText, len(stored))
+	for i, msg := range stored {
+		converted[i] = RoleText{Role: msg.Role, Text: msg.Content}
+	}
+	return converted
+}
+
+func (s *GeminiWebState) findConversationByMetadata(model string, metadata []string) ([]RoleText, bool) {
+	if len(metadata) == 0 {
+		return nil, false
+	}
+	s.convMu.RLock()
+	defer s.convMu.RUnlock()
+	for _, rec := range s.convData {
+		if !strings.EqualFold(strings.TrimSpace(rec.Model), strings.TrimSpace(model)) {
+			continue
+		}
+		if !equalStringSlice(rec.Metadata, metadata) {
+			continue
+		}
+		return cloneRoleTextSlice(storedMessagesToRoleText(rec.Messages)), true
+	}
+	return nil, false
+}
+
 func (s *GeminiWebState) GetRequestMutex() *sync.Mutex { return &s.reqMu }
 
 func (s *GeminiWebState) EnsureClient() error {
@@ -248,7 +326,7 @@ func (s *GeminiWebState) prepare(ctx context.Context, modelName string, rawJSON
 		return nil, &interfaces.ErrorMessage{StatusCode: 400, Error: fmt.Errorf("bad request: %w", err)}
 	}
 	cleaned := SanitizeAssistantMessages(messages)
-	res.cleaned = cleaned
+	fullCleaned := cloneRoleTextSlice(cleaned)
 	res.underlying = MapAliasToUnderlying(modelName)
 	model, err := ModelFromName(res.underlying)
 	if err != nil {
@@ -261,18 +339,27 @@ func (s *GeminiWebState) prepare(ctx context.Context, modelName string, rawJSON
 	mimesSubset := mimes
 
 	if s.useReusableContext() {
-		reuseMeta, remaining := s.reuseFromPending(res.underlying, cleaned)
-		if len(reuseMeta) == 0 {
-			reuseMeta, remaining = s.findReusableSession(res.underlying, cleaned)
+		reusePlan := s.reuseFromPending(res.underlying, cleaned)
+		if reusePlan == nil {
+			reusePlan = s.findReusableSession(res.underlying, cleaned)
 		}
-		if len(reuseMeta) > 0 {
+		if reusePlan != nil {
 			res.reuse = true
-			meta = reuseMeta
-			if len(remaining) == 1 {
-				useMsgs = []RoleText{remaining[0]}
-			} else if len(remaining) > 1 {
-				useMsgs = remaining
-			} else if len(cleaned) > 0 {
+			meta = cloneStringSlice(reusePlan.metadata)
+			overlap := reusePlan.overlap
+			if overlap > len(cleaned) {
+				overlap = len(cleaned)
+			} else if overlap < 0 {
+				overlap = 0
+			}
+			delta := cloneRoleTextSlice(cleaned[overlap:])
+			if len(reusePlan.history) > 0 {
+				fullCleaned = append(cloneRoleTextSlice(reusePlan.history), delta...)
+			} else {
+				fullCleaned = append(cloneRoleTextSlice(cleaned[:overlap]), delta...)
+			}
+			useMsgs = delta
+			if len(delta) == 0 && len(cleaned) > 0 {
 				useMsgs = []RoleText{cleaned[len(cleaned)-1]}
 			}
 			if len(useMsgs) == 1 && len(messages) > 0 && len(msgFileIdx) == len(messages) {
@@ -330,6 +417,8 @@ func (s *GeminiWebState) prepare(ctx context.Context, modelName string, rawJSON
 		s.convMu.RUnlock()
 	}
 
+	res.cleaned = fullCleaned
+
 	res.tagged = NeedRoleTags(useMsgs)
 	if res.reuse && len(useMsgs) == 1 {
 		res.tagged = false
@@ -533,33 +622,44 @@ func (s *GeminiWebState) useReusableContext() bool {
 	return s.cfg.GeminiWeb.Context
 }
 
-func (s *GeminiWebState) reuseFromPending(modelName string, msgs []RoleText) ([]string, []RoleText) {
+func (s *GeminiWebState) reuseFromPending(modelName string, msgs []RoleText) *reuseComputation {
 	match := s.consumePendingMatch()
 	if match == nil {
-		return nil, nil
+		return nil
 	}
 	if !strings.EqualFold(strings.TrimSpace(match.Model), strings.TrimSpace(modelName)) {
-		return nil, nil
+		return nil
 	}
-	prefixLen := match.Record.PrefixLen
-	if prefixLen <= 0 || prefixLen > len(msgs) {
-		return nil, nil
-	}
-	metadata := match.Record.Metadata
+	metadata := cloneStringSlice(match.Record.Metadata)
 	if len(metadata) == 0 {
-		return nil, nil
+		return nil
 	}
-	remaining := make([]RoleText, len(msgs)-prefixLen)
-	copy(remaining, msgs[prefixLen:])
-	return metadata, remaining
+	history, ok := s.findConversationByMetadata(modelName, metadata)
+	if !ok {
+		return nil
+	}
+	overlap := longestHistoryOverlap(history, msgs)
+	return &reuseComputation{metadata: metadata, history: history, overlap: overlap}
 }
 
-func (s *GeminiWebState) findReusableSession(modelName string, msgs []RoleText) ([]string, []RoleText) {
+func (s *GeminiWebState) findReusableSession(modelName string, msgs []RoleText) *reuseComputation {
 	s.convMu.RLock()
 	items := s.convData
 	index := s.convIndex
 	s.convMu.RUnlock()
-	return FindReusableSessionIn(items, index, s.stableClientID, s.accountID, modelName, msgs)
+	rec, metadata, overlap, ok := FindReusableSessionIn(items, index, s.stableClientID, s.accountID, modelName, msgs)
+	if !ok {
+		return nil
+	}
+	history := cloneRoleTextSlice(storedMessagesToRoleText(rec.Messages))
+	if len(history) == 0 {
+		return nil
+	}
+	// Ensure overlap reflects the actual history alignment.
+	if computed := longestHistoryOverlap(history, msgs); computed > 0 {
+		overlap = computed
+	}
+	return &reuseComputation{metadata: cloneStringSlice(metadata), history: history, overlap: overlap}
 }
 
 func (s *GeminiWebState) getConfiguredGem() *Gem {
@@ -865,9 +965,9 @@ func FindConversationIn(items map[string]ConversationRecord, index map[string]st
 }
 
 // FindReusableSessionIn returns reusable metadata and the remaining message suffix.
-func FindReusableSessionIn(items map[string]ConversationRecord, index map[string]string, stableClientID, email, model string, msgs []RoleText) ([]string, []RoleText) {
+func FindReusableSessionIn(items map[string]ConversationRecord, index map[string]string, stableClientID, email, model string, msgs []RoleText) (ConversationRecord, []string, int, bool) {
 	if len(msgs) < 2 {
-		return nil, nil
+		return ConversationRecord{}, nil, 0, false
 	}
 	searchEnd := len(msgs)
 	for searchEnd >= 2 {
@@ -875,11 +975,10 @@ func FindReusableSessionIn(items map[string]ConversationRecord, index map[string
 		tail := sub[len(sub)-1]
 		if strings.EqualFold(tail.Role, "assistant") || strings.EqualFold(tail.Role, "system") {
 			if rec, ok := FindConversationIn(items, index, stableClientID, email, model, sub); ok {
-				remain := msgs[searchEnd:]
-				return rec.Metadata, remain
+				return rec, rec.Metadata, searchEnd, true
 			}
 		}
 		searchEnd--
 	}
-	return nil, nil
+	return ConversationRecord{}, nil, 0, false
 }