diff --git a/pkg/agent/context.go b/pkg/agent/context.go
index 5a84c45e2..1708d8a10 100644
--- a/pkg/agent/context.go
+++ b/pkg/agent/context.go
@@ -614,6 +614,26 @@ func sanitizeHistoryForProvider(history []providers.Message) []providers.Message
 			sanitized = append(sanitized, msg)
 
 		case "assistant":
+			if len(msg.ToolCalls) > 0 {
+				// Normalize tool calls: restores Name from Function.Name after JSON
+				// deserialization (Name is json:"-" and is lost when sessions are
+				// persisted). Drop any tool calls that still have an empty name or
+				// ID after normalization — these would cause Anthropic API errors
+				// ("tooluse.name: String should have at least 1 character").
+				cleaned := make([]providers.ToolCall, 0, len(msg.ToolCalls))
+				for _, tc := range msg.ToolCalls {
+					tc = providers.NormalizeToolCall(tc)
+					if strings.TrimSpace(tc.ID) == "" || strings.TrimSpace(tc.Name) == "" {
+						logger.DebugCF("agent", "Dropping tool call with empty id or name", map[string]any{
+							"id":   tc.ID,
+							"name": tc.Name,
+						})
+						continue
+					}
+					cleaned = append(cleaned, tc)
+				}
+				msg.ToolCalls = cleaned
+			}
 			if len(msg.ToolCalls) > 0 {
 				if len(sanitized) == 0 {
 					logger.DebugCF("agent", "Dropping assistant tool-call turn at history start", map[string]any{})
@@ -640,6 +660,9 @@ func sanitizeHistoryForProvider(history []providers.Message) []providers.Message
 	// tool result messages following it. This is required by strict providers
 	// like DeepSeek that enforce: "An assistant message with 'tool_calls' must
 	// be followed by tool messages responding to each 'tool_call_id'."
+	// Also drops tool results whose ToolCallID has no matching tool call in the
+	// preceding assistant message (can occur when some tool calls were dropped
+	// by the normalization step above).
 	final := make([]providers.Message, 0, len(sanitized))
 	for i := 0; i < len(sanitized); i++ {
 		msg := sanitized[i]
@@ -650,13 +673,13 @@ func sanitizeHistoryForProvider(history []providers.Message) []providers.Message
 				expected[tc.ID] = false
 			}
 
-			// Check following messages for matching tool results
-			toolMsgCount := 0
+			// Collect following tool messages
+			var toolMsgs []providers.Message
 			for j := i + 1; j < len(sanitized); j++ {
 				if sanitized[j].Role != "tool" {
 					break
 				}
-				toolMsgCount++
+				toolMsgs = append(toolMsgs, sanitized[j])
 				if _, exists := expected[sanitized[j].ToolCallID]; exists {
 					expected[sanitized[j].ToolCallID] = true
 				}
@@ -673,7 +696,7 @@ func sanitizeHistoryForProvider(history []providers.Message) []providers.Message
 						map[string]any{
 							"missing_tool_call_id": toolCallID,
 							"expected_count":       len(expected),
-							"found_count":          toolMsgCount,
+							"found_count":          len(toolMsgs),
 						},
 					)
 					break
@@ -682,9 +705,25 @@ func sanitizeHistoryForProvider(history []providers.Message) []providers.Message
 
 			if !allFound {
 				// Skip this assistant message and its tool messages
-				i += toolMsgCount
+				i += len(toolMsgs)
 				continue
 			}
+
+			// Add the assistant message, then only tool results that match an
+			// expected tool call ID. Drop orphaned results (referencing a tool
+			// call that was removed by the normalization step above).
+			final = append(final, msg)
+			for _, tm := range toolMsgs {
+				if expected[tm.ToolCallID] {
+					final = append(final, tm)
+				} else {
+					logger.DebugCF("agent", "Dropping tool result with no matching tool call", map[string]any{
+						"tool_call_id": tm.ToolCallID,
+					})
+				}
+			}
+			i += len(toolMsgs)
+			continue
 		}
 		final = append(final, msg)
 	}
diff --git a/pkg/agent/context_test.go b/pkg/agent/context_test.go
index 5756ed911..1e37e3fca 100644
--- a/pkg/agent/context_test.go
+++ b/pkg/agent/context_test.go
@@ -13,7 +13,15 @@ func msg(role, content string) providers.Message {
 func assistantWithTools(toolIDs ...string) providers.Message {
 	calls := make([]providers.ToolCall, len(toolIDs))
 	for i, id := range toolIDs {
-		calls[i] = providers.ToolCall{ID: id, Type: "function"}
+		calls[i] = providers.ToolCall{
+			ID:   id,
+			Type: "function",
+			Name: "test_tool",
+			Function: &providers.FunctionCall{
+				Name:      "test_tool",
+				Arguments: "{}",
+			},
+		}
 	}
 	return providers.Message{Role: "assistant", ToolCalls: calls}
 }
@@ -281,3 +289,76 @@ func TestSanitizeHistoryForProvider_PartialToolResultsInMiddle(t *testing.T) {
 	}
 	assertRoles(t, result, "user", "assistant", "tool", "assistant", "user", "user", "assistant", "tool", "assistant")
 }
+
+// TestSanitizeHistoryForProvider_EmptyToolCallName tests that tool calls with
+// an empty name are dropped. This can occur when sessions are deserialized from
+// JSON storage: ToolCall.Name is json:"-" so it is lost, but Function.Name is
+// preserved. NormalizeToolCall restores Name from Function.Name; tool calls
+// where both are empty are dropped to prevent "tooluse.name: String should
+// have at least 1 character" errors from the Anthropic API.
+func TestSanitizeHistoryForProvider_EmptyToolCallName(t *testing.T) {
+	// Tool call with empty Name but Function.Name set — should be normalized and kept.
+	toolCallRestorable := providers.ToolCall{
+		ID:   "A",
+		Type: "function",
+		// Name intentionally empty (simulates post-JSON-deserialization state)
+		Function: &providers.FunctionCall{Name: "my_tool", Arguments: "{}"},
+	}
+	// Tool call with both Name and Function.Name empty — truly invalid, should be dropped.
+	toolCallInvalid := providers.ToolCall{
+		ID:   "B",
+		Type: "function",
+		// Name empty, Function.Name empty
+		Function: &providers.FunctionCall{Name: "", Arguments: "{}"},
+	}
+
+	history := []providers.Message{
+		msg("user", "hello"),
+		{Role: "assistant", ToolCalls: []providers.ToolCall{toolCallRestorable, toolCallInvalid}},
+		toolResult("A"),
+		toolResult("B"), // orphaned result for the dropped tool call
+	}
+
+	result := sanitizeHistoryForProvider(history)
+	// toolCallRestorable: Name restored from Function.Name → kept.
+	// toolCallInvalid: Name still empty after normalization → dropped.
+	// toolResult("B") references the dropped call → also dropped.
+	// Result: user, assistant (with only tc_A), tool_A
+	if len(result) != 3 {
+		t.Fatalf("expected 3 messages, got %d: %+v", len(result), roles(result))
+	}
+	assertRoles(t, result, "user", "assistant", "tool")
+	if len(result[1].ToolCalls) != 1 {
+		t.Fatalf("expected 1 tool call in assistant, got %d", len(result[1].ToolCalls))
+	}
+	if result[1].ToolCalls[0].Name != "my_tool" {
+		t.Errorf("expected tool call name %q, got %q", "my_tool", result[1].ToolCalls[0].Name)
+	}
+	if result[2].ToolCallID != "A" {
+		t.Errorf("expected surviving tool result id %q, got %q", "A", result[2].ToolCallID)
+	}
+}
+
+// TestSanitizeHistoryForProvider_EmptyToolCallID tests that tool calls with an
+// empty ID are dropped (an empty ID also causes Anthropic API errors).
+func TestSanitizeHistoryForProvider_EmptyToolCallID(t *testing.T) {
+	history := []providers.Message{
+		msg("user", "hello"),
+		{Role: "assistant", ToolCalls: []providers.ToolCall{
+			{ID: "", Name: "my_tool", Type: "function", Function: &providers.FunctionCall{Name: "my_tool"}},
+		}},
+		// No tool result since the call has no ID to reference
+	}
+
+	result := sanitizeHistoryForProvider(history)
+	// The tool call with empty ID is dropped; the assistant message has no tool
+	// calls after filtering, so it passes through as a plain assistant message.
+	// user + assistant (plain) = 2
+	if len(result) != 2 {
+		t.Fatalf("expected 2 messages, got %d: %+v", len(result), roles(result))
+	}
+	assertRoles(t, result, "user", "assistant")
+	if len(result[1].ToolCalls) != 0 {
+		t.Fatalf("expected 0 tool calls in assistant, got %d", len(result[1].ToolCalls))
+	}
+}