diff --git a/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.spec.ts b/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.spec.ts
index 28cc39a4..54c81f38 100644
--- a/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.spec.ts
+++ b/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.spec.ts
@@ -55,4 +55,11 @@ describe('ChatCheckpointMarkerComponent', () => {
     (fx.nativeElement.querySelector('[data-action="fork"]') as HTMLButtonElement).click();
     expect(fx.componentInstance.forked).toEqual(['cp-1']);
   });
+
+  it('positions the host as a containing block so the hover pill anchors to the dot', () => {
+    const fx = TestBed.createComponent(HostComponent);
+    fx.detectChanges();
+    const host = fx.nativeElement.querySelector('chat-checkpoint-marker') as HTMLElement;
+    expect(getComputedStyle(host).position).toBe('relative');
+  });
 });
diff --git a/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.ts b/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.ts
index f7d15a66..0e81c266 100644
--- a/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.ts
+++ b/libs/chat/src/lib/primitives/chat-checkpoint-marker/chat-checkpoint-marker.component.ts
@@ -16,6 +16,7 @@ import { CHAT_HOST_TOKENS } from '../../styles/chat-tokens';
       width: 14px;
       height: 100%;
       flex: 0 0 14px;
+      position: relative;
     }
     .chat-checkpoint-marker__dot {
       width: 10px;
diff --git a/libs/chat/src/lib/primitives/chat-confirm-dialog/chat-confirm-dialog.component.spec.ts b/libs/chat/src/lib/primitives/chat-confirm-dialog/chat-confirm-dialog.component.spec.ts
index 9a58b89c..184dca84 100644
--- a/libs/chat/src/lib/primitives/chat-confirm-dialog/chat-confirm-dialog.component.spec.ts
+++ b/libs/chat/src/lib/primitives/chat-confirm-dialog/chat-confirm-dialog.component.spec.ts
@@ -3,6 +3,7 @@
 import { TestBed } from '@angular/core/testing';
 import { describe, expect, it } from 'vitest';
 import { ChatConfirmDialogComponent } from './chat-confirm-dialog.component';
+import { CHAT_CONFIRM_DIALOG_STYLES } from '../../styles/chat-confirm-dialog.styles';
 
 function render(opts: {
   open?: boolean;
@@ -89,6 +90,19 @@ describe('ChatConfirmDialogComponent', () => {
     expect(confirm.classList.contains('chat-confirm-dialog__confirm--destructive')).toBe(true);
   });
 
+  it('destructive confirm button uses the new --ngaf-chat-destructive token, not --ngaf-chat-error-text', () => {
+    // Regression guard: error-text is light pink (#fca5a5) in dark mode, which gave
+    // white-text-on-pink unreadable contrast. The destructive button must use a
+    // dedicated token that resolves to a saturated red on both themes.
+    expect(CHAT_CONFIRM_DIALOG_STYLES).toContain('.chat-confirm-dialog__confirm--destructive');
+    const destructiveBlock = CHAT_CONFIRM_DIALOG_STYLES
+      .split('.chat-confirm-dialog__confirm--destructive')
+      .slice(1)
+      .join('.chat-confirm-dialog__confirm--destructive');
+    expect(destructiveBlock).toContain('var(--ngaf-chat-destructive)');
+    expect(destructiveBlock).not.toContain('var(--ngaf-chat-error-text)');
+  });
+
   it('confirm button has labelled text from confirmLabel input', () => {
     const fixture = render({ confirmLabel: 'Yes do it' });
     const confirm = fixture.nativeElement.querySelector('.chat-confirm-dialog__confirm');
diff --git a/libs/chat/src/lib/styles/chat-confirm-dialog.styles.ts b/libs/chat/src/lib/styles/chat-confirm-dialog.styles.ts
index 96293c3d..eecdbda6 100644
--- a/libs/chat/src/lib/styles/chat-confirm-dialog.styles.ts
+++ b/libs/chat/src/lib/styles/chat-confirm-dialog.styles.ts
@@ -59,8 +59,12 @@ export const CHAT_CONFIRM_DIALOG_STYLES = `
     border-color: transparent;
   }
   .chat-confirm-dialog__confirm--destructive {
-    background: var(--ngaf-chat-error-text);
+    background: var(--ngaf-chat-destructive);
     color: #fff;
+    border-color: transparent;
+  }
+  .chat-confirm-dialog__confirm--destructive:hover {
+    filter: brightness(1.1);
   }
   .chat-confirm-dialog__cancel:focus-visible,
   .chat-confirm-dialog__confirm:focus-visible {
diff --git a/libs/chat/src/lib/styles/chat-sidenav.styles.ts b/libs/chat/src/lib/styles/chat-sidenav.styles.ts
index e6f67f53..37caea2c 100644
--- a/libs/chat/src/lib/styles/chat-sidenav.styles.ts
+++ b/libs/chat/src/lib/styles/chat-sidenav.styles.ts
@@ -151,10 +151,10 @@ export const CHAT_SIDENAV_STYLES = `
   }
   .chat-sidenav__threads-heading {
     padding: 8px 12px 4px;
-    font-size: var(--ngaf-chat-font-size-xs);
+    font-size: 11px;
     color: var(--ngaf-chat-text-muted);
     text-transform: uppercase;
-    letter-spacing: 0.05em;
+    letter-spacing: 0.4px;
   }
   :host([data-mode="collapsed"]) .chat-sidenav__threads-heading {
     display: none;
@@ -178,9 +178,9 @@ export const CHAT_SIDENAV_STYLES = `
     background: transparent;
     color: var(--ngaf-chat-text-muted);
     font: inherit;
-    font-size: var(--ngaf-chat-font-size-xs);
+    font-size: 11px;
     text-transform: uppercase;
-    letter-spacing: 0.05em;
+    letter-spacing: 0.4px;
     text-align: left;
     cursor: pointer;
   }
diff --git a/libs/chat/src/lib/styles/chat-tokens.ts b/libs/chat/src/lib/styles/chat-tokens.ts
index 2438b0aa..f3c5dde1 100644
--- a/libs/chat/src/lib/styles/chat-tokens.ts
+++ b/libs/chat/src/lib/styles/chat-tokens.ts
@@ -14,6 +14,7 @@ const LIGHT_TOKENS = `
   --ngaf-chat-error-bg: #fef2f2;
   --ngaf-chat-error-border: #fecaca;
   --ngaf-chat-error-text: #dc2626;
+  --ngaf-chat-destructive: #dc2626;
   --ngaf-chat-warning-bg: #fffbeb;
   --ngaf-chat-warning-text: #b45309;
   --ngaf-chat-success: #16a34a;
@@ -35,6 +36,7 @@ const DARK_TOKENS = `
   --ngaf-chat-error-bg: rgb(45, 21, 21);
   --ngaf-chat-error-border: #dc2626;
   --ngaf-chat-error-text: #fca5a5;
+  --ngaf-chat-destructive: #ef4444;
   --ngaf-chat-warning-bg: rgb(45, 35, 21);
   --ngaf-chat-warning-text: #fbbf24;
   --ngaf-chat-success: #4ade80;
diff --git a/libs/chat/src/lib/styles/chat.css b/libs/chat/src/lib/styles/chat.css
index 7c75afa1..bc0b5107 100644
--- a/libs/chat/src/lib/styles/chat.css
+++ b/libs/chat/src/lib/styles/chat.css
@@ -27,6 +27,7 @@
   --ngaf-chat-error-bg: #fef2f2;
   --ngaf-chat-error-border: #fecaca;
   --ngaf-chat-error-text: #dc2626;
+  --ngaf-chat-destructive: #dc2626;
   --ngaf-chat-warning-bg: #fffbeb;
   --ngaf-chat-warning-text: #b45309;
   --ngaf-chat-success: #16a34a;
@@ -157,6 +158,7 @@
     --ngaf-chat-error-bg: rgb(45, 21, 21);
     --ngaf-chat-error-border: #dc2626;
     --ngaf-chat-error-text: #fca5a5;
+    --ngaf-chat-destructive: #ef4444;
     --ngaf-chat-warning-bg: rgb(45, 35, 21);
     --ngaf-chat-warning-text: #fbbf24;
     --ngaf-chat-success: #4ade80;
@@ -176,6 +178,7 @@
   --ngaf-chat-error-bg: rgb(45, 21, 21);
   --ngaf-chat-error-border: #dc2626;
   --ngaf-chat-error-text: #fca5a5;
+  --ngaf-chat-destructive: #ef4444;
   --ngaf-chat-warning-bg: rgb(45, 35, 21);
   --ngaf-chat-warning-text: #fbbf24;
   --ngaf-chat-success: #4ade80;