diff --git a/.jules/bolt.md b/.jules/bolt.md
index d54cf10fc..469dd8c61 100644
--- a/.jules/bolt.md
+++ b/.jules/bolt.md
@@ -61,3 +61,6 @@
 ## 2026-07-13 - Array.from mapping optimization
 **Learning:** Using `Array.from({ length: N }).map(...)` creates an intermediate array of `undefined` values which requires memory allocation and garbage collection, adding O(N) unnecessary overhead in frequently re-rendered UI components.
 **Action:** Use `Array.from({ length: N }, (_, index) => ...)` to map elements directly during array creation, avoiding intermediate allocations.
+## 2024-05-14 - Python O(N^2) list dedup bottleneck
+**Learning:** Found O(N^2) deduplication using `if item not in list:` inside nested loops in `services/analysis-engine/src/bandscope_analysis/exports/chart.py`. Given that memory instructions suggest using dictionary keys for deduplication (`dict.fromkeys(items)` or `seen[item] = None`) to maintain O(1) lookups and preserve insertion order, this is a measurable performance anti-pattern.
+**Action:** Replace `item not in list` with dict key lookups (`dict.fromkeys()` where applicable, or a `seen` dict) in hot paths like export and formatting routines.
diff --git a/services/analysis-engine/src/bandscope_analysis/exports/chart.py b/services/analysis-engine/src/bandscope_analysis/exports/chart.py
index 3a84b59c8..6d853bf0b 100644
--- a/services/analysis-engine/src/bandscope_analysis/exports/chart.py
+++ b/services/analysis-engine/src/bandscope_analysis/exports/chart.py
@@ -79,11 +79,13 @@ def _active_role_ids(section: Mapping[str, object]) -> list[str] | None:
     if not isinstance(part_graph, list):
         return None
     active: list[str] = []
+    seen: set[str] = set()
     for node in part_graph:
         if not isinstance(node, Mapping) or node.get("is_active") is not True:
             continue
         role_id = node.get("role_id")
-        if isinstance(role_id, str) and role_id and role_id not in active:
+        if isinstance(role_id, str) and role_id and role_id not in seen:
+            seen.add(role_id)
             active.append(role_id)
     return active
 
@@ -122,9 +124,12 @@ def _role_display_name(role: Mapping[str, object]) -> str | None:
 def _active_role_names(section: Mapping[str, object]) -> list[str]:
     """Return de-duplicated display names for the section's active roles."""
     names: list[str] = []
+    # Use expected O(1) dictionary membership instead of O(N) list membership.
+    seen: dict[str, None] = {}
     for role in _active_roles(section):
         name = _role_display_name(role)
-        if name is not None and name not in names:
+        if name is not None and name not in seen:
+            seen[name] = None
             names.append(name)
     return names
 
@@ -132,12 +137,15 @@ def _active_role_names(section: Mapping[str, object]) -> list[str]:
 def _section_cue(section: Mapping[str, object]) -> str:
     """Join the active roles' cue values into a single cue string."""
     cues: list[str] = []
+    # Use expected O(1) dictionary membership instead of O(N) list membership.
+    seen: dict[str, None] = {}
     for role in _active_roles(section):
         cue = role.get("cue")
         if not isinstance(cue, Mapping):
             continue
         value = cue.get("value")
-        if isinstance(value, str) and value and value not in cues:
+        if isinstance(value, str) and value and value not in seen:
+            seen[value] = None
             cues.append(value)
     return "; ".join(cues)
 
@@ -189,6 +197,8 @@ def _footer_lines(song: Mapping[str, object], sections: list[Mapping[str, object
     """Build the footer: per-role rehearsal priorities and the export focus."""
     lines: list[str] = []
     priorities: list[str] = []
+    # Use expected O(1) dictionary membership instead of O(N) list membership.
+    seen_priorities: dict[str, None] = {}
     for section in sections:
         for role in _section_roles(section):
             name = _role_display_name(role)
@@ -196,7 +206,8 @@ def _footer_lines(song: Mapping[str, object], sections: list[Mapping[str, object
             if name is None or not isinstance(priority, str) or not priority:
                 continue
             entry = f"  - {name}: {priority}"
-            if entry not in priorities:
+            if entry not in seen_priorities:
+                seen_priorities[entry] = None
                 priorities.append(entry)
     if priorities:
         lines.append("Priorities:")
diff --git a/services/analysis-engine/tests/test_chart_export_dedup_complexity.py b/services/analysis-engine/tests/test_chart_export_dedup_complexity.py
new file mode 100644
index 000000000..b47ee1459
--- /dev/null
+++ b/services/analysis-engine/tests/test_chart_export_dedup_complexity.py
@@ -0,0 +1,37 @@
+"""Deterministic complexity regression for chart-export role de-duplication."""
+
+from typing import ClassVar
+
+from bandscope_analysis.exports.chart import _active_role_ids
+
+
+class _CountingRoleId(str):
+    """String role id that counts equality work without wall-clock timing."""
+
+    comparisons: ClassVar[int] = 0
+
+    def __eq__(self, other: object) -> bool:
+        """Count one equality comparison and preserve normal string semantics."""
+        type(self).comparisons += 1
+        return super().__eq__(other)
+
+    def __hash__(self) -> int:
+        """Preserve normal string hashing for representative hash membership."""
+        return super().__hash__()
+
+
+def test_active_role_id_deduplication_avoids_quadratic_equality_work() -> None:
+    """Unique active ids must not require pairwise list-membership comparisons."""
+    role_ids = [_CountingRoleId(f"role-{index}") for index in range(64)]
+    section = {
+        "partGraph": [
+            {"role_id": role_id, "is_active": True}
+            for role_id in [*role_ids, _CountingRoleId("role-0")]
+        ]
+    }
+
+    _CountingRoleId.comparisons = 0
+    active = _active_role_ids(section)
+
+    assert active == role_ids
+    assert _CountingRoleId.comparisons < 256