diff --git a/SKILL.md b/SKILL.md
index 0903d36e..2f588cc0 100644
--- a/SKILL.md
+++ b/SKILL.md
@@ -39,9 +39,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -167,7 +165,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/bin/gstack-telemetry-log b/bin/gstack-telemetry-log
index d8ea84d6..edcbdbab 100755
--- a/bin/gstack-telemetry-log
+++ b/bin/gstack-telemetry-log
@@ -21,7 +21,7 @@ GSTACK_DIR="${GSTACK_DIR:-$(cd "$(dirname "$0")/.." && pwd)}"
 STATE_DIR="${GSTACK_STATE_DIR:-$HOME/.gstack}"
 ANALYTICS_DIR="$STATE_DIR/analytics"
 JSONL_FILE="$ANALYTICS_DIR/skill-usage.jsonl"
-PENDING_FILE="$ANALYTICS_DIR/.pending"
+PENDING_DIR="$ANALYTICS_DIR"  # .pending-* files live here
 CONFIG_CMD="$GSTACK_DIR/bin/gstack-config"
 VERSION_FILE="$GSTACK_DIR/VERSION"
 
@@ -58,16 +58,23 @@ case "$TIER" in
 esac
 
 if [ "$TIER" = "off" ]; then
-  # Still clear any pending marker even if telemetry is off
-  rm -f "$PENDING_FILE" 2>/dev/null || true
+  # Still clear pending markers for this session even if telemetry is off
+  [ -n "$SESSION_ID" ] && rm -f "$PENDING_DIR/.pending-$SESSION_ID" 2>/dev/null || true
   exit 0
 fi
 
-# ─── Finalize stale .pending marker ─────────────────────────
-if [ -f "$PENDING_FILE" ]; then
-  # .pending contains a JSON fragment: {"skill":"X","ts":"Y","session_id":"Z","gstack_version":"V"}
-  PENDING_DATA="$(cat "$PENDING_FILE" 2>/dev/null || true)"
-  rm -f "$PENDING_FILE" 2>/dev/null || true
+# ─── Finalize stale .pending markers ────────────────────────
+# Each session gets its own .pending-$SESSION_ID file to avoid races
+# between concurrent sessions. Finalize any that don't match our session.
+for PFILE in "$PENDING_DIR"/.pending-*; do
+  [ -f "$PFILE" ] || continue
+  # Skip our own session's marker (it's still in-flight)
+  PFILE_BASE="$(basename "$PFILE")"
+  PFILE_SID="${PFILE_BASE#.pending-}"
+  [ "$PFILE_SID" = "$SESSION_ID" ] && continue
+
+  PENDING_DATA="$(cat "$PFILE" 2>/dev/null || true)"
+  rm -f "$PFILE" 2>/dev/null || true
   if [ -n "$PENDING_DATA" ]; then
     # Extract fields from pending marker using grep -o + awk
     P_SKILL="$(echo "$PENDING_DATA" | grep -o '"skill":"[^"]*"' | head -1 | awk -F'"' '{print $4}')"
@@ -82,7 +89,10 @@ if [ -f "$PENDING_FILE" ]; then
     printf '{"v":1,"ts":"%s","event_type":"skill_run","skill":"%s","session_id":"%s","gstack_version":"%s","os":"%s","arch":"%s","duration_s":null,"outcome":"unknown","error_class":null,"used_browse":false,"sessions":1}\n' \
       "$P_TS" "$P_SKILL" "$P_SID" "$P_VER" "$P_OS" "$P_ARCH" >> "$JSONL_FILE" 2>/dev/null || true
   fi
-fi
+done
+
+# Clear our own session's pending marker (we're about to log the real event)
+[ -n "$SESSION_ID" ] && rm -f "$PENDING_DIR/.pending-$SESSION_ID" 2>/dev/null || true
 
 # ─── Collect metadata ────────────────────────────────────────
 TS="$(date -u +%Y-%m-%dT%H:%M:%SZ 2>/dev/null || date -u +%Y-%m-%dT%H:%M:%S 2>/dev/null || echo "")"
diff --git a/browse/SKILL.md b/browse/SKILL.md
index 3c61abef..306b2fe6 100644
--- a/browse/SKILL.md
+++ b/browse/SKILL.md
@@ -40,9 +40,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -168,7 +166,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/design-consultation/SKILL.md b/design-consultation/SKILL.md
index aa21fba4..792ad553 100644
--- a/design-consultation/SKILL.md
+++ b/design-consultation/SKILL.md
@@ -43,9 +43,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -171,7 +169,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/design-review/SKILL.md b/design-review/SKILL.md
index 52ea3773..a86663d1 100644
--- a/design-review/SKILL.md
+++ b/design-review/SKILL.md
@@ -43,9 +43,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -171,7 +169,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/document-release/SKILL.md b/document-release/SKILL.md
index 12f1d239..e252c86b 100644
--- a/document-release/SKILL.md
+++ b/document-release/SKILL.md
@@ -41,9 +41,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -169,7 +167,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/plan-ceo-review/SKILL.md b/plan-ceo-review/SKILL.md
index 9b749407..b0aebbb5 100644
--- a/plan-ceo-review/SKILL.md
+++ b/plan-ceo-review/SKILL.md
@@ -41,9 +41,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -169,7 +167,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/plan-design-review/SKILL.md b/plan-design-review/SKILL.md
index 8a46b277..00d34731 100644
--- a/plan-design-review/SKILL.md
+++ b/plan-design-review/SKILL.md
@@ -41,9 +41,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -169,7 +167,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/plan-eng-review/SKILL.md b/plan-eng-review/SKILL.md
index b10c2b56..3eb94197 100644
--- a/plan-eng-review/SKILL.md
+++ b/plan-eng-review/SKILL.md
@@ -40,9 +40,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -168,7 +166,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/qa-only/SKILL.md b/qa-only/SKILL.md
index 628eef03..5cb39530 100644
--- a/qa-only/SKILL.md
+++ b/qa-only/SKILL.md
@@ -38,9 +38,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -166,7 +164,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/qa/SKILL.md b/qa/SKILL.md
index 21405b3b..051f00d9 100644
--- a/qa/SKILL.md
+++ b/qa/SKILL.md
@@ -44,9 +44,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -172,7 +170,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/retro/SKILL.md b/retro/SKILL.md
index fd26249b..8f8a7957 100644
--- a/retro/SKILL.md
+++ b/retro/SKILL.md
@@ -39,9 +39,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -167,7 +165,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/review/SKILL.md b/review/SKILL.md
index 0fae854e..e7f0b6b4 100644
--- a/review/SKILL.md
+++ b/review/SKILL.md
@@ -40,9 +40,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -168,7 +166,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/scripts/gen-skill-docs.ts b/scripts/gen-skill-docs.ts
index 6055a890..5024c9e8 100644
--- a/scripts/gen-skill-docs.ts
+++ b/scripts/gen-skill-docs.ts
@@ -118,9 +118,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: \${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 \`\`\`
 
 If \`PROACTIVE\` is \`"false"\`, do not proactively suggest gstack skills — only invoke
@@ -246,7 +244,7 @@ interrupted). Run this bash:
 \`\`\`bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \\
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \\
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/setup-browser-cookies/SKILL.md b/setup-browser-cookies/SKILL.md
index bd497f99..9f54786d 100644
--- a/setup-browser-cookies/SKILL.md
+++ b/setup-browser-cookies/SKILL.md
@@ -37,9 +37,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -165,7 +163,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/ship/SKILL.md b/ship/SKILL.md
index dc18ef84..b9c12887 100644
--- a/ship/SKILL.md
+++ b/ship/SKILL.md
@@ -39,9 +39,7 @@ _SESSION_ID="$$-$(date +%s)"
 echo "TELEMETRY: ${_TEL:-off}"
 echo "TEL_PROMPTED: $_TEL_PROMPTED"
 mkdir -p ~/.gstack/analytics
-if [ -f ~/.gstack/analytics/.pending ]; then
-  ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown 2>/dev/null || true
-fi
+for _PF in ~/.gstack/analytics/.pending-* 2>/dev/null; do [ -f "$_PF" ] && ~/.claude/skills/gstack/bin/gstack-telemetry-log --event-type skill_run --skill _pending_finalize --outcome unknown --session-id "$_SESSION_ID" 2>/dev/null || true; break; done
 ```
 
 If `PROACTIVE` is `"false"`, do not proactively suggest gstack skills — only invoke
@@ -167,7 +165,7 @@ interrupted). Run this bash:
 ```bash
 _TEL_END=$(date +%s)
 _TEL_DUR=$(( _TEL_END - _TEL_START ))
-rm -f ~/.gstack/analytics/.pending 2>/dev/null || true
+rm -f ~/.gstack/analytics/.pending-"$_SESSION_ID" 2>/dev/null || true
 ~/.claude/skills/gstack/bin/gstack-telemetry-log \
   --skill "SKILL_NAME" --duration "$_TEL_DUR" --outcome "OUTCOME" \
   --used-browse "USED_BROWSE" --session-id "$_SESSION_ID" 2>/dev/null &
diff --git a/supabase/migrations/001_telemetry.sql b/supabase/migrations/001_telemetry.sql
index b41275f1..2febf4ed 100644
--- a/supabase/migrations/001_telemetry.sql
+++ b/supabase/migrations/001_telemetry.sql
@@ -60,14 +60,15 @@ CREATE VIEW crash_clusters AS
 SELECT
   error_class,
   gstack_version,
-  COUNT(*) as count,
-  COUNT(DISTINCT installation_id) as unique_users,
+  COUNT(*) as total_occurrences,
+  COUNT(DISTINCT installation_id) as identified_users,  -- community tier only
+  COUNT(*) - COUNT(installation_id) as anonymous_occurrences,  -- events without installation_id
   MIN(event_timestamp) as first_seen,
   MAX(event_timestamp) as last_seen
 FROM telemetry_events
 WHERE outcome = 'error' AND error_class IS NOT NULL
 GROUP BY error_class, gstack_version
-ORDER BY count DESC;
+ORDER BY total_occurrences DESC;
 
 -- Skill sequence co-occurrence view
 CREATE VIEW skill_sequences AS
diff --git a/test/telemetry.test.ts b/test/telemetry.test.ts
index 8fadfdd4..ec516b83 100644
--- a/test/telemetry.test.ts
+++ b/test/telemetry.test.ts
@@ -139,18 +139,18 @@ describe('gstack-telemetry-log', () => {
 });
 
 describe('.pending marker', () => {
-  test('finalizes stale .pending as outcome:unknown', () => {
+  test('finalizes stale .pending from another session as outcome:unknown', () => {
     setConfig('telemetry', 'anonymous');
 
-    // Write a fake .pending marker
+    // Write a fake .pending marker from a different session
     const analyticsDir = path.join(tmpDir, 'analytics');
     fs.mkdirSync(analyticsDir, { recursive: true });
     fs.writeFileSync(
-      path.join(analyticsDir, '.pending'),
+      path.join(analyticsDir, '.pending-old-123'),
       '{"skill":"old-skill","ts":"2026-03-18T00:00:00Z","session_id":"old-123","gstack_version":"0.6.4"}'
     );
 
-    // Run telemetry-log — should finalize the pending marker first
+    // Run telemetry-log with a DIFFERENT session — should finalize the old pending marker
     run(`${BIN}/gstack-telemetry-log --skill qa --duration 50 --outcome success --session-id new-456`);
 
     const events = parseJsonl();
@@ -166,26 +166,43 @@ describe('.pending marker', () => {
     expect(events[1].outcome).toBe('success');
   });
 
-  test('.pending file is removed after finalization', () => {
+  test('.pending-SESSION file is removed after finalization', () => {
     setConfig('telemetry', 'anonymous');
 
     const analyticsDir = path.join(tmpDir, 'analytics');
     fs.mkdirSync(analyticsDir, { recursive: true });
-    const pendingPath = path.join(analyticsDir, '.pending');
-    fs.writeFileSync(pendingPath, '{"skill":"stale","ts":"2026-03-18T00:00:00Z","session_id":"s","gstack_version":"v"}');
+    const pendingPath = path.join(analyticsDir, '.pending-stale-session');
+    fs.writeFileSync(pendingPath, '{"skill":"stale","ts":"2026-03-18T00:00:00Z","session_id":"stale-session","gstack_version":"v"}');
 
     run(`${BIN}/gstack-telemetry-log --skill qa --duration 50 --outcome success --session-id new-456`);
 
     expect(fs.existsSync(pendingPath)).toBe(false);
   });
 
-  test('tier=off still clears .pending', () => {
+  test('does not finalize own session pending marker', () => {
+    setConfig('telemetry', 'anonymous');
+
+    const analyticsDir = path.join(tmpDir, 'analytics');
+    fs.mkdirSync(analyticsDir, { recursive: true });
+    // Create pending for same session ID we'll use
+    const pendingPath = path.join(analyticsDir, '.pending-same-session');
+    fs.writeFileSync(pendingPath, '{"skill":"in-flight","ts":"2026-03-18T00:00:00Z","session_id":"same-session","gstack_version":"v"}');
+
+    run(`${BIN}/gstack-telemetry-log --skill qa --duration 50 --outcome success --session-id same-session`);
+
+    // Should only have 1 event (the new one), not finalize own pending
+    const events = parseJsonl();
+    expect(events).toHaveLength(1);
+    expect(events[0].skill).toBe('qa');
+  });
+
+  test('tier=off still clears own session pending', () => {
     setConfig('telemetry', 'off');
 
     const analyticsDir = path.join(tmpDir, 'analytics');
     fs.mkdirSync(analyticsDir, { recursive: true });
-    const pendingPath = path.join(analyticsDir, '.pending');
-    fs.writeFileSync(pendingPath, '{"skill":"stale","ts":"2026-03-18T00:00:00Z","session_id":"s","gstack_version":"v"}');
+    const pendingPath = path.join(analyticsDir, '.pending-off-123');
+    fs.writeFileSync(pendingPath, '{"skill":"stale","ts":"2026-03-18T00:00:00Z","session_id":"off-123","gstack_version":"v"}');
 
     run(`${BIN}/gstack-telemetry-log --skill qa --duration 50 --outcome success --session-id off-123`);