diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Initial-Rendering-should-render-settings-list-with-visual-indicators.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Initial-Rendering-should-render-settings-list-with-visual-indicators.snap.svg
index 96ac9e7621..b4d435477a 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Initial-Rendering-should-render-settings-list-with-visual-indicators.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Initial-Rendering-should-render-settings-list-with-visual-indicators.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-accessibility-settings-enabled-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-accessibility-settings-enabled-correctly.snap.svg
index 7a35e051b2..4c7dd1001c 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-accessibility-settings-enabled-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-accessibility-settings-enabled-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-all-boolean-settings-disabled-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-all-boolean-settings-disabled-correctly.snap.svg
index 9c01031ebe..ac64bd5295 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-all-boolean-settings-disabled-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-all-boolean-settings-disabled-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false*
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-default-state-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-default-state-correctly.snap.svg
index 96ac9e7621..b4d435477a 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-default-state-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-default-state-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-file-filtering-settings-configured-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-file-filtering-settings-configured-correctly.snap.svg
index 96ac9e7621..b4d435477a 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-file-filtering-settings-configured-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-file-filtering-settings-configured-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-focused-on-scope-selector-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-focused-on-scope-selector-correctly.snap.svg
index f9cf782f72..cc297389e3 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-focused-on-scope-selector-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-focused-on-scope-selector-correctly.snap.svg
@@ -83,20 +83,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-mixed-boolean-and-number-settings-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-mixed-boolean-and-number-settings-correctly.snap.svg
index 1866d1ab67..3b66401a58 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-mixed-boolean-and-number-settings-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-mixed-boolean-and-number-settings-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-tools-and-security-settings-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-tools-and-security-settings-correctly.snap.svg
index 96ac9e7621..b4d435477a 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-tools-and-security-settings-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-tools-and-security-settings-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- false
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-various-boolean-settings-enabled-correctly.snap.svg b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-various-boolean-settings-enabled-correctly.snap.svg
index 739a96cf09..73a29bd34f 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-various-boolean-settings-enabled-correctly.snap.svg
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog-SettingsDialog-Snapshot-Tests-should-render-various-boolean-settings-enabled-correctly.snap.svg
@@ -94,20 +94,20 @@
│
│
│
- Max Chat Model Attempts
- 10
+ Clear Context on Plan Approval
+ undefined
│
│
- Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
+ Automatically clear conversation context after a plan is approved and implement…
│
│
│
│
- Debug Keystroke Logging
- true*
+ Max Chat Model Attempts
+ 10
│
│
- Enable debug logging of keystrokes to the console.
+ Maximum number of attempts for requests to the main chat model. Cannot exceed 10.
│
│
│
diff --git a/packages/cli/src/ui/components/__snapshots__/SettingsDialog.test.tsx.snap b/packages/cli/src/ui/components/__snapshots__/SettingsDialog.test.tsx.snap
index be2dd8d9a2..59682bb004 100644
--- a/packages/cli/src/ui/components/__snapshots__/SettingsDialog.test.tsx.snap
+++ b/packages/cli/src/ui/components/__snapshots__/SettingsDialog.test.tsx.snap
@@ -28,12 +28,12 @@ exports[`SettingsDialog > Initial Rendering > should render settings list with v
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -74,12 +74,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'accessibility settings
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -120,12 +120,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'all boolean settings d
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false* │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -166,12 +166,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'default state' correct
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -212,12 +212,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'file filtering setting
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -258,12 +258,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'focused on scope selec
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ > Apply To │
@@ -304,12 +304,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'mixed boolean and numb
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -350,12 +350,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'tools and security set
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging false │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │
@@ -396,12 +396,12 @@ exports[`SettingsDialog > Snapshot Tests > should render 'various boolean settin
│ Plan Model Routing true │
│ Automatically switch between Pro and Flash models based on Plan Mode status. Uses Pr… │
│ │
+│ Clear Context on Plan Approval undefined │
+│ Automatically clear conversation context after a plan is approved and implement… │
+│ │
│ Max Chat Model Attempts 10 │
│ Maximum number of attempts for requests to the main chat model. Cannot exceed 10. │
│ │
-│ Debug Keystroke Logging true* │
-│ Enable debug logging of keystrokes to the console. │
-│ │
│ ▼ │
│ │
│ Apply To │