diff --git a/ContextCompactor.cs b/ContextCompactor.cs
index 0bbda8b..a325a7f 100644
--- a/ContextCompactor.cs
+++ b/ContextCompactor.cs
@@ -34,7 +34,7 @@ internal sealed partial class ContextCompactor(IChatClient client)
     {
         int compacted = 0;
         int userTurnsSeen = 0;
-        var filesRead = new HashSet<string>(StringComparer.OrdinalIgnoreCase);
+        Dictionary<string, int> filesRead = new(StringComparer.OrdinalIgnoreCase);
 
         // Walk backwards: index 0 is system prompt, so we stop at 1.
         for (int i = history.Count - 1; i >= 1; i--)
@@ -71,10 +71,10 @@ internal sealed partial class ContextCompactor(IChatClient client)
                                 string reason = "";
 
                                 // Rule 1: Deduplication. If we have already seen this file in a newer message (since we are walking backward), redact this one.
-                                if (filesRead.Contains(filePath))
+                                if (filesRead.TryGetValue(filePath, out int count) && count >= 3)
                                 {
                                     shouldRedact = true;
-                                    reason = "deduplication — you read this file again later";
+                                    reason = "deduplication — you read this file 3 or more times later";
                                 }
                                 // Rule 2: TTL. If this was read 2 or more user turns ago, redact it.
                                 else if (userTurnsSeen >= 2)
@@ -92,7 +92,7 @@ internal sealed partial class ContextCompactor(IChatClient client)
                                 else
                                 {
                                     // Keep it, but mark that we've seen it so older reads of the same file are redacted.
-                                    filesRead.Add(filePath);
+                                    filesRead[filePath] = filesRead.GetValueOrDefault(filePath) + 1;
                                 }
                             }
                         }