diff --git a/agent/context_compressor.py b/agent/context_compressor.py
index 93158cee8f81..ee4d7af29858 100644
--- a/agent/context_compressor.py
+++ b/agent/context_compressor.py
@@ -1728,8 +1728,10 @@ This compaction should PRIORITISE preserving all information related to the focu
                         "multiple times across this summary and the protected "
                         "messages above/below (successive compactions). "
                         "Reloading a skill **once** is sufficient — it remains "
-                        "in context for the rest of the session. Do not reload "
-                        "the same skill multiple times."
+                        "in context for the rest of the session. "
+                        "After reloading, **ignore any remaining [SKILL_PRUNED] markers "
+                        "for that skill** — they are historical artifacts from previous "
+                        "compactions and do not need further action."
                     )
             # Store for iterative updates on next compaction
             self._previous_summary = summary
diff --git a/agent/prompt_builder.py b/agent/prompt_builder.py
index 2ced932efd34..69482c8c02bc 100644
--- a/agent/prompt_builder.py
+++ b/agent/prompt_builder.py
@@ -180,7 +180,8 @@ SKILLS_GUIDANCE = (
     "## Skill Safety Rule\n"
     "1. **UNAVAILABLE** — If a skill placeholder contains `[SKILL_PRUNED]`, the skill content was lost in compression and is inaccessible.\n"
     "2. **RELOAD** — Before performing any action that depends on a skill, re-check its content with `skill_view(name='...')` if it shows `[SKILL_PRUNED]`.\n"
-    "3. **WAIT** — If a skill is loading or was just pruned, wait for the reload confirmation before proceeding."
+    "3. **WAIT** — If a skill is loading or was just pruned, wait for the reload confirmation before proceeding.\n"
+    "4. **DEDUP** — After reloading a pruned skill, **ignore any remaining `[SKILL_PRUNED]` markers for that same skill** — they are historical artifacts from previous compactions and do not need further action.\n"
 )
 
 KANBAN_GUIDANCE = (