diff --git a/agent/model_metadata.py b/agent/model_metadata.py
index 3af2e7bafb..03f70b3fe4 100644
--- a/agent/model_metadata.py
+++ b/agent/model_metadata.py
@@ -1045,16 +1045,21 @@ def get_model_context_length(
 
 
 def estimate_tokens_rough(text: str) -> int:
-    """Rough token estimate (~4 chars/token) for pre-flight checks."""
+    """Rough token estimate (~4 chars/token) for pre-flight checks.
+
+    Uses ceiling division so short texts (1-3 chars) never estimate as
+    0 tokens, which would cause the compressor and pre-flight checks to
+    systematically undercount when many short tool results are present.
+    """
     if not text:
         return 0
-    return len(text) // 4
+    return (len(text) + 3) // 4
 
 
 def estimate_messages_tokens_rough(messages: List[Dict[str, Any]]) -> int:
     """Rough token estimate for a message list (pre-flight only)."""
     total_chars = sum(len(str(msg)) for msg in messages)
-    return total_chars // 4
+    return (total_chars + 3) // 4
 
 
 def estimate_request_tokens_rough(
@@ -1077,4 +1082,4 @@ def estimate_request_tokens_rough(
         total_chars += sum(len(str(msg)) for msg in messages)
     if tools:
         total_chars += len(str(tools))
-    return total_chars // 4
+    return (total_chars + 3) // 4
diff --git a/run_agent.py b/run_agent.py
index bc4ad2754b..7b97c0ded2 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -8049,7 +8049,7 @@ class AIAgent:
 
             # Calculate approximate request size for logging
             total_chars = sum(len(str(msg)) for msg in api_messages)
-            approx_tokens = total_chars // 4  # Rough estimate: 4 chars per token
+            approx_tokens = estimate_messages_tokens_rough(api_messages)
             
             # Thinking spinner for quiet mode (animated during API call)
             thinking_spinner = None
diff --git a/tests/agent/test_model_metadata.py b/tests/agent/test_model_metadata.py
index 1eac37e20f..df680fb241 100644
--- a/tests/agent/test_model_metadata.py
+++ b/tests/agent/test_model_metadata.py
@@ -50,7 +50,8 @@ class TestEstimateTokensRough:
         assert estimate_tokens_rough("a" * 400) == 100
 
     def test_short_text(self):
-        assert estimate_tokens_rough("hello") == 1
+        # "hello" = 5 chars → ceil(5/4) = 2
+        assert estimate_tokens_rough("hello") == 2
 
     def test_proportional(self):
         short = estimate_tokens_rough("hello world")
@@ -68,10 +69,11 @@ class TestEstimateMessagesTokensRough:
         assert estimate_messages_tokens_rough([]) == 0
 
     def test_single_message_concrete_value(self):
-        """Verify against known str(msg) length."""
+        """Verify against known str(msg) length (ceiling division)."""
         msg = {"role": "user", "content": "a" * 400}
         result = estimate_messages_tokens_rough([msg])
-        expected = len(str(msg)) // 4
+        n = len(str(msg))
+        expected = (n + 3) // 4
         assert result == expected
 
     def test_multiple_messages_additive(self):
@@ -80,7 +82,8 @@ class TestEstimateMessagesTokensRough:
             {"role": "assistant", "content": "Hi there, how can I help?"},
         ]
         result = estimate_messages_tokens_rough(msgs)
-        expected = sum(len(str(m)) for m in msgs) // 4
+        n = sum(len(str(m)) for m in msgs)
+        expected = (n + 3) // 4
         assert result == expected
 
     def test_tool_call_message(self):
@@ -89,7 +92,7 @@ class TestEstimateMessagesTokensRough:
                "tool_calls": [{"id": "1", "function": {"name": "terminal", "arguments": "{}"}}]}
         result = estimate_messages_tokens_rough([msg])
         assert result > 0
-        assert result == len(str(msg)) // 4
+        assert result == (len(str(msg)) + 3) // 4
 
     def test_message_with_list_content(self):
         """Vision messages with multimodal content arrays."""
@@ -98,7 +101,7 @@ class TestEstimateMessagesTokensRough:
             {"type": "image_url", "image_url": {"url": "data:image/png;base64,AAAA"}}
         ]}
         result = estimate_messages_tokens_rough([msg])
-        assert result == len(str(msg)) // 4
+        assert result == (len(str(msg)) + 3) // 4
 
 
 # =========================================================================