diff --git a/pkg/agent/context_seahorse_test.go b/pkg/agent/context_seahorse_test.go
index e405ef94..05c83183 100644
--- a/pkg/agent/context_seahorse_test.go
+++ b/pkg/agent/context_seahorse_test.go
@@ -280,6 +280,74 @@ func TestSeahorseToProviderMessagesWithToolCalls(t *testing.T) {
 	}
 }
 
+func TestSeahorseAssemblePreservesActiveToolTurnAcrossSanitization(t *testing.T) {
+	engine, err := seahorse.NewEngine(seahorse.Config{
+		DBPath: t.TempDir() + "/seahorse.db",
+	}, nil)
+	if err != nil {
+		t.Fatalf("NewEngine: %v", err)
+	}
+
+	ctx := context.Background()
+	sessionKey := "test:active-tool-turn"
+	_, err = engine.Ingest(ctx, sessionKey, []seahorse.Message{
+		{
+			Role:       "assistant",
+			Content:    "older context",
+			TokenCount: 20,
+		},
+		{
+			Role:       "user",
+			Content:    "inspect the file",
+			TokenCount: 5,
+		},
+		{
+			Role:       "assistant",
+			TokenCount: 5,
+			Parts: []seahorse.MessagePart{{
+				Type:       "tool_use",
+				Name:       "read_file",
+				Arguments:  `{"path":"/tmp/test.txt"}`,
+				ToolCallID: "tc_1",
+			}},
+		},
+		{
+			Role:       "tool",
+			TokenCount: 200,
+			Parts: []seahorse.MessagePart{{
+				Type:       "tool_result",
+				ToolCallID: "tc_1",
+				Text:       "very large tool output",
+			}},
+		},
+		{
+			Role:       "assistant",
+			Content:    "done",
+			TokenCount: 5,
+		},
+	})
+	if err != nil {
+		t.Fatalf("Ingest: %v", err)
+	}
+
+	result, err := engine.Assemble(ctx, sessionKey, seahorse.AssembleInput{Budget: 210})
+	if err != nil {
+		t.Fatalf("Assemble: %v", err)
+	}
+
+	sanitized := sanitizeHistoryForProvider(seahorseToProviderMessages(result))
+	if len(sanitized) != 4 {
+		t.Fatalf("sanitized history len = %d, want 4 protected-turn messages", len(sanitized))
+	}
+	assertRoles(t, sanitized, "user", "assistant", "tool", "assistant")
+	if len(sanitized[1].ToolCalls) != 1 || sanitized[1].ToolCalls[0].ID != "tc_1" {
+		t.Fatalf("assistant tool calls = %+v, want preserved tool call tc_1", sanitized[1].ToolCalls)
+	}
+	if sanitized[2].ToolCallID != "tc_1" {
+		t.Fatalf("tool result id = %q, want tc_1", sanitized[2].ToolCallID)
+	}
+}
+
 func TestSeahorseToProviderMessagesToolResult(t *testing.T) {
 	msg := seahorse.Message{
 		Role:       "tool",
diff --git a/pkg/seahorse/short_assembler.go b/pkg/seahorse/short_assembler.go
index 0bfd66a6..5533512a 100644
--- a/pkg/seahorse/short_assembler.go
+++ b/pkg/seahorse/short_assembler.go
@@ -68,24 +68,33 @@ func (a *Assembler) Assemble(ctx context.Context, convID int64, input AssembleIn
 		freshTailTokens += r.tokenCount
 	}
 
-	// If the protected tail alone exceeds budget, trim from the oldest end of
-	// the tail until the newest items fit within the requested budget.
+	// If the protected tail alone exceeds budget, trim from the oldest end at
+	// provider-safe boundaries. The rebuild path later sanitizes leading
+	// assistant(tool_calls)/tool messages, so splitting the active turn here can
+	// silently discard the very context we are trying to protect.
 	if freshTailTokens > input.Budget {
 		originalTailCount := len(freshTail)
 		originalFreshTailTokens := freshTailTokens
-		for freshTailTokens > input.Budget && len(freshTail) > 0 {
-			freshTailTokens -= freshTail[0].tokenCount
-			freshTail = freshTail[1:]
-		}
-		logger.InfoCF("seahorse", "assemble: trimmed fresh tail to budget", map[string]any{
+		var preservedActiveTurn bool
+		freshTail, freshTailTokens, preservedActiveTurn = trimFreshTailToSafeBudget(freshTail, input.Budget)
+		logFields := map[string]any{
 			"budget":                input.Budget,
 			"fresh_tail_tokens":     freshTailTokens,
 			"fresh_tail_count":      len(freshTail),
 			"trimmed_fresh_items":   originalTailCount - len(freshTail),
 			"original_fresh_tokens": originalFreshTailTokens,
-		})
+			"preserved_active_turn": preservedActiveTurn,
+		}
+		if preservedActiveTurn {
+			logger.WarnCF("seahorse", "assemble: preserving active turn over budget", logFields)
+		} else {
+			logger.InfoCF("seahorse", "assemble: trimmed fresh tail to safe boundary", logFields)
+		}
 	}
 	remainingBudget := input.Budget - freshTailTokens
+	if remainingBudget < 0 {
+		remainingBudget = 0
+	}
 
 	var selected []resolvedItem
 	evictableTokens := 0
@@ -189,6 +198,81 @@ func (a *Assembler) Assemble(ctx context.Context, convID int64, input AssembleIn
 	}, nil
 }
 
+func trimFreshTailToSafeBudget(tail []resolvedItem, budget int) ([]resolvedItem, int, bool) {
+	tailTokens := resolvedItemsTokenCount(tail)
+	if tailTokens <= budget {
+		return tail, tailTokens, false
+	}
+
+	latestTurnStart := lastUserMessageIndex(tail)
+	if latestTurnStart >= 0 {
+		latestTurnTokens := resolvedItemsTokenCount(tail[latestTurnStart:])
+		if latestTurnTokens > budget {
+			return tail[latestTurnStart:], latestTurnTokens, true
+		}
+	}
+
+	start := 0
+	for tailTokens > budget && start < len(tail) {
+		tailTokens -= tail[start].tokenCount
+		start++
+	}
+	for start < len(tail) && !isProviderSafeHistoryStart(tail[start:]) {
+		tailTokens -= tail[start].tokenCount
+		start++
+	}
+
+	return tail[start:], tailTokens, false
+}
+
+func resolvedItemsTokenCount(items []resolvedItem) int {
+	total := 0
+	for _, item := range items {
+		total += item.tokenCount
+	}
+	return total
+}
+
+func lastUserMessageIndex(items []resolvedItem) int {
+	for i := len(items) - 1; i >= 0; i-- {
+		if items[i].itemType != "message" || items[i].message == nil {
+			continue
+		}
+		if items[i].message.Role == "user" {
+			return i
+		}
+	}
+	return -1
+}
+
+func isProviderSafeHistoryStart(items []resolvedItem) bool {
+	for _, item := range items {
+		if item.itemType != "message" || item.message == nil {
+			continue
+		}
+		if item.message.Role == "tool" {
+			return false
+		}
+		if item.message.Role == "assistant" && messageHasToolUse(item.message) {
+			return false
+		}
+		return true
+	}
+	return true
+}
+
+func messageHasToolUse(msg *Message) bool {
+	if msg == nil {
+		return false
+	}
+	for _, part := range msg.Parts {
+		if part.Type == "tool_use" {
+			return true
+		}
+	}
+	return false
+}
+
 // resolveItem loads the full message or summary for a context item.
 func (a *Assembler) resolveItem(ctx context.Context, item ContextItem) (resolvedItem, error) {
 	if item.ItemType == "message" {
diff --git a/pkg/seahorse/short_assembler_test.go b/pkg/seahorse/short_assembler_test.go
index 81918afa..6472bc36 100644
--- a/pkg/seahorse/short_assembler_test.go
+++ b/pkg/seahorse/short_assembler_test.go
@@ -171,6 +171,68 @@ func TestAssemblerBudgetEvictsOldest(t *testing.T) {
 	}
 }
 
+func TestAssemblerBudgetPreservesLatestToolTurnWhenItExceedsBudget(t *testing.T) {
+	s, convID := setupAssemblerStore(t)
+	ctx := context.Background()
+
+	oldMsg, _ := s.AddMessage(ctx, convID, "assistant", "older context", 20)
+	userMsg, _ := s.AddMessage(ctx, convID, "user", "inspect the file", 5)
+	assistantToolMsg, _ := s.AddMessageWithParts(ctx, convID, "assistant", []MessagePart{
+		{
+			Type:       "tool_use",
+			Name:       "read_file",
+			Arguments:  `{"path":"/tmp/test.txt"}`,
+			ToolCallID: "tc_1",
+		},
+	}, 5)
+	toolResultMsg, _ := s.AddMessageWithParts(ctx, convID, "tool", []MessagePart{
+		{
+			Type:       "tool_result",
+			ToolCallID: "tc_1",
+			Text:       "very large tool output",
+		},
+	}, 200)
+	finalAssistantMsg, _ := s.AddMessage(ctx, convID, "assistant", "done", 5)
+
+	s.UpsertContextItems(ctx, convID, []ContextItem{
+		{Ordinal: 100, ItemType: "message", MessageID: oldMsg.ID, TokenCount: 20},
+		{Ordinal: 200, ItemType: "message", MessageID: userMsg.ID, TokenCount: 5},
+		{Ordinal: 300, ItemType: "message", MessageID: assistantToolMsg.ID, TokenCount: 5},
+		{Ordinal: 400, ItemType: "message", MessageID: toolResultMsg.ID, TokenCount: 200},
+		{Ordinal: 500, ItemType: "message", MessageID: finalAssistantMsg.ID, TokenCount: 5},
+	})
+
+	a := &Assembler{store: s, config: Config{}}
+	result, err := a.Assemble(ctx, convID, AssembleInput{Budget: 210})
+	if err != nil {
+		t.Fatalf("Assemble: %v", err)
+	}
+
+	if len(result.Messages) != 4 {
+		t.Fatalf("Messages = %d, want 4 protected-turn messages", len(result.Messages))
+	}
+	if result.Messages[0].ID != userMsg.ID {
+		t.Fatalf("first message ID = %d, want current user message %d", result.Messages[0].ID, userMsg.ID)
+	}
+	if result.Messages[1].ID != assistantToolMsg.ID {
+		t.Fatalf("second message ID = %d, want assistant tool-call %d", result.Messages[1].ID, assistantToolMsg.ID)
+	}
+	if result.Messages[2].ID != toolResultMsg.ID {
+		t.Fatalf("third message ID = %d, want tool result %d", result.Messages[2].ID, toolResultMsg.ID)
+	}
+	if result.Messages[3].ID != finalAssistantMsg.ID {
+		t.Fatalf("fourth message ID = %d, want final assistant %d", result.Messages[3].ID, finalAssistantMsg.ID)
+	}
+
+	totalTokens := 0
+	for _, msg := range result.Messages {
+		totalTokens += msg.TokenCount
+	}
+	if totalTokens <= 210 {
+		t.Fatalf("assembled tokens = %d, want protected turn to remain over budget", totalTokens)
+	}
+}
+
 func TestAssemblerBudgetFitsAll(t *testing.T) {
 	s, convID := setupAssemblerStore(t)
 	ctx := context.Background()