diff --git a/SKILL.md b/SKILL.md
index 9849e78f..1eeeff2f 100644
--- a/SKILL.md
+++ b/SKILL.md
@@ -62,6 +62,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -179,6 +182,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/autoplan/SKILL.md b/autoplan/SKILL.md
index 7831d0b4..c831c835 100644
--- a/autoplan/SKILL.md
+++ b/autoplan/SKILL.md
@@ -71,6 +71,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -271,6 +274,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/benchmark/SKILL.md b/benchmark/SKILL.md
index 92914083..abfa24da 100644
--- a/benchmark/SKILL.md
+++ b/benchmark/SKILL.md
@@ -64,6 +64,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -181,6 +184,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/browse/SKILL.md b/browse/SKILL.md
index d97d737d..36fc8989 100644
--- a/browse/SKILL.md
+++ b/browse/SKILL.md
@@ -64,6 +64,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -181,6 +184,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/canary/SKILL.md b/canary/SKILL.md
index a711689d..5e245bae 100644
--- a/canary/SKILL.md
+++ b/canary/SKILL.md
@@ -64,6 +64,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -246,6 +249,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/codex/SKILL.md b/codex/SKILL.md
index ea365776..f01bcba2 100644
--- a/codex/SKILL.md
+++ b/codex/SKILL.md
@@ -65,6 +65,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -265,6 +268,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/connect-chrome/SKILL.md b/connect-chrome/SKILL.md
index fe0d14e6..5084c0e0 100644
--- a/connect-chrome/SKILL.md
+++ b/connect-chrome/SKILL.md
@@ -62,6 +62,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -262,6 +265,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/cso/SKILL.md b/cso/SKILL.md
index 77b11979..f5dbca09 100644
--- a/cso/SKILL.md
+++ b/cso/SKILL.md
@@ -68,6 +68,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -250,6 +253,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/design-consultation/SKILL.md b/design-consultation/SKILL.md
index cc73ec6a..91325e11 100644
--- a/design-consultation/SKILL.md
+++ b/design-consultation/SKILL.md
@@ -69,6 +69,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -269,6 +272,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/design-review/SKILL.md b/design-review/SKILL.md
index 2e0b1d17..31519c55 100644
--- a/design-review/SKILL.md
+++ b/design-review/SKILL.md
@@ -69,6 +69,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -269,6 +272,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/design-shotgun/SKILL.md b/design-shotgun/SKILL.md
index 3ebd118e..a4dbaa88 100644
--- a/design-shotgun/SKILL.md
+++ b/design-shotgun/SKILL.md
@@ -66,6 +66,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -248,6 +251,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/document-release/SKILL.md b/document-release/SKILL.md
index 0fe79991..c4f840b6 100644
--- a/document-release/SKILL.md
+++ b/document-release/SKILL.md
@@ -66,6 +66,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -248,6 +251,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/investigate/SKILL.md b/investigate/SKILL.md
index 1dba6b97..bab696b1 100644
--- a/investigate/SKILL.md
+++ b/investigate/SKILL.md
@@ -80,6 +80,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -262,6 +265,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
@@ -528,7 +549,8 @@ this session, log it for future sessions:
 ```
 
 **Types:** `pattern` (reusable approach), `pitfall` (what NOT to do), `preference`
-(user stated), `architecture` (structural decision), `tool` (library/framework insight).
+(user stated), `architecture` (structural decision), `tool` (library/framework insight),
+`operational` (project environment/CLI/workflow knowledge).
 
 **Sources:** `observed` (you found this in the code), `user-stated` (user told you),
 `inferred` (AI deduction), `cross-model` (both Claude and Codex agree).
diff --git a/land-and-deploy/SKILL.md b/land-and-deploy/SKILL.md
index 99768441..7d40518c 100644
--- a/land-and-deploy/SKILL.md
+++ b/land-and-deploy/SKILL.md
@@ -63,6 +63,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -263,6 +266,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/learn/SKILL.md b/learn/SKILL.md
index 6172e1b7..f23f89ff 100644
--- a/learn/SKILL.md
+++ b/learn/SKILL.md
@@ -66,6 +66,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -248,6 +251,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/office-hours/SKILL.md b/office-hours/SKILL.md
index b46e9f60..323a63b0 100644
--- a/office-hours/SKILL.md
+++ b/office-hours/SKILL.md
@@ -71,6 +71,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -271,6 +274,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/plan-ceo-review/SKILL.md b/plan-ceo-review/SKILL.md
index b3ac1b25..cffd8747 100644
--- a/plan-ceo-review/SKILL.md
+++ b/plan-ceo-review/SKILL.md
@@ -69,6 +69,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -269,6 +272,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/plan-design-review/SKILL.md b/plan-design-review/SKILL.md
index af43a069..a7479bf9 100644
--- a/plan-design-review/SKILL.md
+++ b/plan-design-review/SKILL.md
@@ -67,6 +67,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -267,6 +270,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/plan-eng-review/SKILL.md b/plan-eng-review/SKILL.md
index badef1f9..5ecd6871 100644
--- a/plan-eng-review/SKILL.md
+++ b/plan-eng-review/SKILL.md
@@ -68,6 +68,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -268,6 +271,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/qa-only/SKILL.md b/qa-only/SKILL.md
index 659571f9..4a538657 100644
--- a/qa-only/SKILL.md
+++ b/qa-only/SKILL.md
@@ -64,6 +64,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -264,6 +267,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/qa/SKILL.md b/qa/SKILL.md
index 57dfe86a..0e03a4c6 100644
--- a/qa/SKILL.md
+++ b/qa/SKILL.md
@@ -70,6 +70,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -270,6 +273,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/retro/SKILL.md b/retro/SKILL.md
index 19b487ee..4d202efa 100644
--- a/retro/SKILL.md
+++ b/retro/SKILL.md
@@ -64,6 +64,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -246,6 +249,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
@@ -621,7 +642,8 @@ this session, log it for future sessions:
 ```
 
 **Types:** `pattern` (reusable approach), `pitfall` (what NOT to do), `preference`
-(user stated), `architecture` (structural decision), `tool` (library/framework insight).
+(user stated), `architecture` (structural decision), `tool` (library/framework insight),
+`operational` (project environment/CLI/workflow knowledge).
 
 **Sources:** `observed` (you found this in the code), `user-stated` (user told you),
 `inferred` (AI deduction), `cross-model` (both Claude and Codex agree).
diff --git a/review/SKILL.md b/review/SKILL.md
index 53835327..6463e80e 100644
--- a/review/SKILL.md
+++ b/review/SKILL.md
@@ -67,6 +67,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -267,6 +270,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
@@ -1190,7 +1211,8 @@ this session, log it for future sessions:
 ```
 
 **Types:** `pattern` (reusable approach), `pitfall` (what NOT to do), `preference`
-(user stated), `architecture` (structural decision), `tool` (library/framework insight).
+(user stated), `architecture` (structural decision), `tool` (library/framework insight),
+`operational` (project environment/CLI/workflow knowledge).
 
 **Sources:** `observed` (you found this in the code), `user-stated` (user told you),
 `inferred` (AI deduction), `cross-model` (both Claude and Codex agree).
diff --git a/scripts/resolvers/learnings.ts b/scripts/resolvers/learnings.ts
index 3bcba7b1..685188fb 100644
--- a/scripts/resolvers/learnings.ts
+++ b/scripts/resolvers/learnings.ts
@@ -80,7 +80,8 @@ ${binDir}/gstack-learnings-log '{"skill":"${ctx.skillName}","type":"TYPE","key":
 \`\`\`
 
 **Types:** \`pattern\` (reusable approach), \`pitfall\` (what NOT to do), \`preference\`
-(user stated), \`architecture\` (structural decision), \`tool\` (library/framework insight).
+(user stated), \`architecture\` (structural decision), \`tool\` (library/framework insight),
+\`operational\` (project environment/CLI/workflow knowledge).
 
 **Sources:** \`observed\` (you found this in the code), \`user-stated\` (user told you),
 \`inferred\` (AI deduction), \`cross-model\` (both Claude and Codex agree).
diff --git a/scripts/resolvers/preamble.ts b/scripts/resolvers/preamble.ts
index 84612925..978bf51c 100644
--- a/scripts/resolvers/preamble.ts
+++ b/scripts/resolvers/preamble.ts
@@ -70,6 +70,9 @@ _LEARN_FILE="\${GSTACK_HOME:-$HOME/.gstack}/projects/\${SLUG:-unknown}/learnings
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ${ctx.paths.binDir}/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -322,7 +325,7 @@ jq -n --arg ts "$(date -u +%Y-%m-%dT%H:%M:%SZ)" --arg skill "SKILL_NAME" --arg b
 \`\`\``;
 }
 
-function generateCompletionStatus(): string {
+function generateCompletionStatus(ctx: TemplateContext): string {
   return `## Completion Status Protocol
 
 When completing a skill workflow, report status using one of:
@@ -348,6 +351,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 \`\`\`
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+\`\`\`bash
+${ctx.paths.binDir}/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+\`\`\`
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
@@ -502,7 +523,7 @@ export function generatePreamble(ctx: TemplateContext): string {
     generateVoiceDirective(tier),
     ...(tier >= 2 ? [generateAskUserFormat(ctx), generateCompletenessSection()] : []),
     ...(tier >= 3 ? [generateRepoModeSection(), generateSearchBeforeBuildingSection(ctx)] : []),
-    generateCompletionStatus(),
+    generateCompletionStatus(ctx),
   ];
   return sections.join('\n\n');
 }
diff --git a/setup-browser-cookies/SKILL.md b/setup-browser-cookies/SKILL.md
index 5c2fe7fe..ea1a5963 100644
--- a/setup-browser-cookies/SKILL.md
+++ b/setup-browser-cookies/SKILL.md
@@ -61,6 +61,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -178,6 +181,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/setup-deploy/SKILL.md b/setup-deploy/SKILL.md
index 79cff939..16e4ab6f 100644
--- a/setup-deploy/SKILL.md
+++ b/setup-deploy/SKILL.md
@@ -67,6 +67,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -249,6 +252,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
diff --git a/ship/SKILL.md b/ship/SKILL.md
index aede6dd5..b801bc79 100644
--- a/ship/SKILL.md
+++ b/ship/SKILL.md
@@ -65,6 +65,9 @@ _LEARN_FILE="${GSTACK_HOME:-$HOME/.gstack}/projects/${SLUG:-unknown}/learnings.j
 if [ -f "$_LEARN_FILE" ]; then
   _LEARN_COUNT=$(wc -l < "$_LEARN_FILE" 2>/dev/null | tr -d ' ')
   echo "LEARNINGS: $_LEARN_COUNT entries loaded"
+  if [ "$_LEARN_COUNT" -gt 5 ] 2>/dev/null; then
+    ~/.claude/skills/gstack/bin/gstack-learnings-search --limit 3 2>/dev/null || true
+  fi
 else
   echo "LEARNINGS: 0"
 fi
@@ -265,6 +268,24 @@ ATTEMPTED: [what you tried]
 RECOMMENDATION: [what the user should do next]
 ```
 
+## Operational Self-Improvement
+
+Before completing, reflect on this session:
+- Did any commands fail unexpectedly?
+- Did you take a wrong approach and have to backtrack?
+- Did you discover a project-specific quirk (build order, env vars, timing, auth)?
+- Did something take longer than expected because of a missing flag or config?
+
+If yes, log an operational learning for future sessions:
+
+```bash
+~/.claude/skills/gstack/bin/gstack-learnings-log '{"skill":"SKILL_NAME","type":"operational","key":"SHORT_KEY","insight":"DESCRIPTION","confidence":N,"source":"observed"}'
+```
+
+Replace SKILL_NAME with the current skill name. Only log genuine operational discoveries.
+Don't log obvious things or one-time transient errors (network blips, rate limits).
+A good test: would knowing this save 5+ minutes in a future session? If yes, log it.
+
 ## Telemetry (run last)
 
 After the skill workflow completes (success, error, or abort), log the telemetry event.
@@ -1662,7 +1683,8 @@ this session, log it for future sessions:
 ```
 
 **Types:** `pattern` (reusable approach), `pitfall` (what NOT to do), `preference`
-(user stated), `architecture` (structural decision), `tool` (library/framework insight).
+(user stated), `architecture` (structural decision), `tool` (library/framework insight),
+`operational` (project environment/CLI/workflow knowledge).
 
 **Sources:** `observed` (you found this in the code), `user-stated` (user told you),
 `inferred` (AI deduction), `cross-model` (both Claude and Codex agree).
diff --git a/test/gen-skill-docs.test.ts b/test/gen-skill-docs.test.ts
index 29162ab1..9dfac539 100644
--- a/test/gen-skill-docs.test.ts
+++ b/test/gen-skill-docs.test.ts
@@ -213,11 +213,20 @@ describe('gen-skill-docs', () => {
     expect(browseTmpl).toContain('{{PREAMBLE}}');
   });
 
-  test('generated SKILL.md contains no contributor mode (removed)', () => {
+  test('generated SKILL.md contains operational self-improvement (replaced contributor mode)', () => {
     const content = fs.readFileSync(path.join(ROOT, 'SKILL.md'), 'utf-8');
     expect(content).not.toContain('Contributor Mode');
     expect(content).not.toContain('gstack_contributor');
     expect(content).not.toContain('contributor-logs');
+    expect(content).toContain('Operational Self-Improvement');
+    expect(content).toContain('gstack-learnings-log');
+    expect(content).toContain('gstack-learnings-search --limit 3');
+  });
+
+  test('generated SKILL.md with LEARNINGS_LOG contains operational type', () => {
+    // Check a skill that has LEARNINGS_LOG (e.g., review)
+    const content = fs.readFileSync(path.join(ROOT, 'review', 'SKILL.md'), 'utf-8');
+    expect(content).toContain('operational');
   });
 
   test('generated SKILL.md contains session awareness', () => {
diff --git a/test/skill-e2e-learnings.test.ts b/test/skill-e2e-learnings.test.ts
index dfd18513..390eedf7 100644
--- a/test/skill-e2e-learnings.test.ts
+++ b/test/skill-e2e-learnings.test.ts
@@ -67,6 +67,11 @@ describeIfSelected('Learnings E2E', ['learnings-show'], () => {
         insight: 'User wants rubocop to run before every commit, no exceptions.',
         confidence: 10, source: 'user-stated', ts: new Date().toISOString(),
       },
+      {
+        skill: 'qa', type: 'operational', key: 'test-timeout-flag',
+        insight: 'bun test requires --timeout 30000 for E2E tests in this project.',
+        confidence: 9, source: 'observed', ts: new Date().toISOString(),
+      },
     ];
 
     fs.writeFileSync(