diff --git a/internal/pipeline/compaction_pending_preservation_test.go b/internal/pipeline/compaction_pending_preservation_test.go
new file mode 100644
index 00000000..e52d09cf
--- /dev/null
+++ b/internal/pipeline/compaction_pending_preservation_test.go
@@ -0,0 +1,131 @@
+package pipeline
+
+import (
+	"context"
+	"errors"
+	"testing"
+
+	"github.com/nextlevelbuilder/goclaw/internal/providers"
+)
+
+// TestPruneStage_Compaction_PreservesPending is the regression guard for the
+// mid-loop compaction tool-pairing bug. ThinkStage appends the current
+// iteration's assistant(tool_calls) message to the pending buffer, then
+// PruneStage runs next. If compaction fires, CompactMessages only receives
+// History() — pending is NOT part of the compaction input — yet ReplaceHistory
+// clears pending. Without preservation, the assistant(tool_calls) message is
+// dropped, ToolStage later appends orphaned tool_result messages, and the next
+// provider call rejects the unpaired tool_result (OpenAI/DeepSeek 400).
+//
+// This test asserts the pending assistant(tool_calls) message survives a
+// mid-loop compaction so tool_calls -> tool_result pairing stays intact.
+func TestPruneStage_Compaction_PreservesPending(t *testing.T) {
+	t.Parallel()
+	// budget = ContextWindow(1000) - overhead(0) - MaxTokens(100) = 900.
+	// History of 50 msgs * 100 tokens = 5000 > 900 forces the compaction path.
+	deps := &PipelineDeps{
+		Config: PipelineConfig{
+			ContextWindow: 1000,
+			MaxTokens:     100,
+		},
+		TokenCounter: &mockTokenCounter{countPerMessage: 100},
+		PruneMessages: func(msgs []providers.Message, _ int) ([]providers.Message, PruneStats) {
+			return msgs, PruneStats{} // no reduction — forces fall-through to compaction
+		},
+		CompactMessages: func(_ context.Context, msgs []providers.Message, _ string) ([]providers.Message, error) {
+			// Compaction summarizes history into a single message. Crucially it
+			// only ever sees History(), never the pending assistant(tool_calls).
+			return []providers.Message{{Role: "user", Content: "[compacted summary]"}}, nil
+		},
+	}
+	stage := NewPruneStage(deps, nil)
+	state := defaultState()
+
+	history := make([]providers.Message, 50)
+	for i := range history {
+		history[i] = providers.Message{Role: "user", Content: "msg"}
+	}
+	state.Messages.SetHistory(history)
+
+	// The in-flight assistant(tool_calls) message ThinkStage placed in pending
+	// this iteration — it must outlive ReplaceHistory.
+	assistantToolCall := providers.Message{
+		Role:      "assistant",
+		ToolCalls: []providers.ToolCall{{ID: "tc-keep", Name: "read_file"}},
+	}
+	state.Messages.AppendPending(assistantToolCall)
+
+	if err := stage.Execute(context.Background(), state); err != nil {
+		t.Fatalf("Execute() error: %v", err)
+	}
+
+	if !state.Prune.MidLoopCompacted {
+		t.Fatal("MidLoopCompacted = false, want true (compaction should have fired)")
+	}
+	if state.Compact.CompactionCount != 1 {
+		t.Errorf("CompactionCount = %d, want 1", state.Compact.CompactionCount)
+	}
+
+	// The assistant(tool_calls) message must still be pending after compaction.
+	pending := state.Messages.Pending()
+	if len(pending) != 1 {
+		t.Fatalf("Pending() len = %d, want 1 (assistant tool_calls preserved across ReplaceHistory)", len(pending))
+	}
+	if pending[0].Role != "assistant" || len(pending[0].ToolCalls) != 1 || pending[0].ToolCalls[0].ID != "tc-keep" {
+		t.Errorf("pending[0] = %+v, want the preserved assistant tool_calls message (id tc-keep)", pending[0])
+	}
+
+	// History should be the compacted summary, not carrying a duplicate of the
+	// preserved pending message.
+	hist := state.Messages.History()
+	if len(hist) != 1 || hist[0].Content != "[compacted summary]" {
+		t.Errorf("History() = %+v, want single compacted summary message", hist)
+	}
+}
+
+// TestThinkStage_EmergencyCompaction_PreservesPending guards the second
+// ReplaceHistory call site. When CallLLM reports a context-overflow error,
+// ThinkStage runs an emergency compaction and retries the iteration. Pending
+// messages already staged this iteration (e.g. iteration-budget nudges from
+// maybeInjectNudge) must survive the ReplaceHistory that emergency compaction
+// performs, for the same reason as the prune path.
+func TestThinkStage_EmergencyCompaction_PreservesPending(t *testing.T) {
+	t.Parallel()
+	deps := &PipelineDeps{
+		Config: PipelineConfig{MaxIterations: 10, MaxTokens: 1000},
+		CallLLM: func(_ context.Context, _ *RunState, _ providers.ChatRequest) (*providers.ChatResponse, error) {
+			// "context length exceeded" is matched by IsContextOverflowMessage.
+			return nil, errors.New("context length exceeded for this request")
+		},
+		CompactMessages: func(_ context.Context, msgs []providers.Message, _ string) ([]providers.Message, error) {
+			return []providers.Message{{Role: "user", Content: "[compacted summary]"}}, nil
+		},
+	}
+	stage := NewThinkStage(deps)
+	state := defaultState()
+	state.Messages.SetHistory([]providers.Message{{Role: "user", Content: "old turn"}})
+
+	// A pending message staged earlier in this iteration (an iteration nudge).
+	nudge := providers.Message{Role: "user", Content: "[System] wrap up your work"}
+	state.Messages.AppendPending(nudge)
+
+	if err := stage.Execute(context.Background(), state); err != nil {
+		t.Fatalf("Execute() error: %v", err)
+	}
+
+	// Emergency compaction retries the iteration (Continue) and records one retry.
+	if stage.Result() != Continue {
+		t.Errorf("Result() = %v, want Continue (retry after emergency compaction)", stage.Result())
+	}
+	if state.Think.OverflowRetries != 1 {
+		t.Errorf("OverflowRetries = %d, want 1", state.Think.OverflowRetries)
+	}
+
+	pending := state.Messages.Pending()
+	if len(pending) != 1 {
+		t.Fatalf("Pending() len = %d, want 1 (nudge preserved across emergency ReplaceHistory)", len(pending))
+	}
+	if pending[0].Content != "[System] wrap up your work" {
+		t.Errorf("pending[0] = %+v, want the preserved nudge message", pending[0])
+	}
+}
diff --git a/internal/pipeline/prune_stage.go b/internal/pipeline/prune_stage.go
index efb35ab1..dca6485a 100644
--- a/internal/pipeline/prune_stage.go
+++ b/internal/pipeline/prune_stage.go
@@ -180,11 +180,21 @@ func (s *PruneStage) Execute(ctx context.Context, state *RunState) error {
 		return nil // no compaction available
 	}
 
+	// Save pending before compaction — ReplaceHistory clears pending,
+	// but pending may contain the current iteration's assistant(tool_calls)
+	// message which must be preserved to maintain tool_calls → tool pairing.
+	savedPending := state.Messages.Pending()
+
 	compacted, err := s.deps.CompactMessages(ctx, state.Messages.History(), state.Model)
 	if err != nil {
 		return fmt.Errorf("compact messages: %w", err)
 	}
 	state.Messages.ReplaceHistory(compacted)
+
+	// Restore pending messages that were cleared by ReplaceHistory.
+	for _, msg := range savedPending {
+		state.Messages.AppendPending(msg)
+	}
 	state.Prune.MidLoopCompacted = true
 	state.Compact.CompactionCount++
 	state.Compact.MemoryFlushedThisCycle = false // reset for next cycle
diff --git a/internal/pipeline/think_stage.go b/internal/pipeline/think_stage.go
index c5dd6640..9ea6383f 100644
--- a/internal/pipeline/think_stage.go
+++ b/internal/pipeline/think_stage.go
@@ -75,9 +75,14 @@ func (s *ThinkStage) Execute(ctx context.Context, state *RunState) error {
 			// Attempt emergency compaction
 			if s.deps.CompactMessages != nil {
 				originalLen := len(state.Messages.History())
+				savedPending := state.Messages.Pending()
 				compacted, compactErr := s.deps.CompactMessages(ctx, state.Messages.History(), state.Model)
 				if compactErr == nil {
 					state.Messages.ReplaceHistory(compacted)
+					// Restore pending cleared by ReplaceHistory.
+					for _, msg := range savedPending {
+						state.Messages.AppendPending(msg)
+					}
 					slog.Info("emergency_compaction_triggered",
 						"run_id", state.RunID,
 						"original_msgs", originalLen,