diff --git a/apps/web/app/custom.css b/apps/web/app/custom.css
index 92c207a4..d24ef7a0 100644
--- a/apps/web/app/custom.css
+++ b/apps/web/app/custom.css
@@ -30,3 +30,12 @@
   background-color: var(--sidebar-accent);
   color: var(--sidebar-accent-foreground);
 }
+
+/* Sonner toast: align icon to first line of text, not vertically centered */
+[data-sonner-toast] {
+  align-items: flex-start !important;
+}
+
+[data-sonner-toast] [data-icon] {
+  margin-top: 2.5px;
+}
diff --git a/apps/web/components/ui/sonner.tsx b/apps/web/components/ui/sonner.tsx
index 9280ee52..cb49e93b 100644
--- a/apps/web/components/ui/sonner.tsx
+++ b/apps/web/components/ui/sonner.tsx
@@ -13,19 +13,19 @@ const Toaster = ({ ...props }: ToasterProps) => {
       className="toaster group"
       icons={{
         success: (
-          <CircleCheckIcon className="size-4" />
+          <CircleCheckIcon className="size-4 text-success" />
         ),
         info: (
-          <InfoIcon className="size-4" />
+          <InfoIcon className="size-4 text-info" />
         ),
         warning: (
-          <TriangleAlertIcon className="size-4" />
+          <TriangleAlertIcon className="size-4 text-warning" />
         ),
         error: (
-          <OctagonXIcon className="size-4" />
+          <OctagonXIcon className="size-4 text-destructive" />
         ),
         loading: (
-          <Loader2Icon className="size-4 animate-spin" />
+          <Loader2Icon className="size-4 animate-spin text-brand" />
         ),
       }}
       style={
diff --git a/apps/web/features/issues/components/agent-live-card.tsx b/apps/web/features/issues/components/agent-live-card.tsx
index 631fea29..173e0d40 100644
--- a/apps/web/features/issues/components/agent-live-card.tsx
+++ b/apps/web/features/issues/components/agent-live-card.tsx
@@ -1,7 +1,7 @@
 "use client";
 
 import { useState, useEffect, useCallback, useRef } from "react";
-import { Bot, ChevronRight, Loader2, ArrowDown, Brain, AlertCircle, Clock, CheckCircle2, XCircle, Square } from "lucide-react";
+import { Bot, ChevronRight, ChevronUp, Loader2, ArrowDown, Brain, AlertCircle, Clock, CheckCircle2, XCircle, Square } from "lucide-react";
 import { api } from "@/shared/api";
 import { useWSEvent } from "@/features/realtime";
 import type { TaskMessagePayload, TaskCompletedPayload, TaskFailedPayload, TaskCancelledPayload } from "@/shared/types/events";
@@ -99,16 +99,20 @@ function buildTimeline(msgs: TaskMessagePayload[]): TimelineItem[] {
 interface AgentLiveCardProps {
   issueId: string;
   agentName?: string;
+  /** Scroll container ref — needed for sticky sentinel detection. */
+  scrollContainerRef?: React.RefObject<HTMLDivElement | null>;
 }
 
-export function AgentLiveCard({ issueId, agentName }: AgentLiveCardProps) {
+export function AgentLiveCard({ issueId, agentName, scrollContainerRef }: AgentLiveCardProps) {
   const { getActorName } = useActorName();
   const [activeTask, setActiveTask] = useState<AgentTask | null>(null);
   const [items, setItems] = useState<TimelineItem[]>([]);
   const [elapsed, setElapsed] = useState("");
   const [autoScroll, setAutoScroll] = useState(true);
   const [cancelling, setCancelling] = useState(false);
+  const [isStuck, setIsStuck] = useState(false);
   const scrollRef = useRef<HTMLDivElement>(null);
+  const sentinelRef = useRef<HTMLDivElement>(null);
   const seenSeqs = useRef(new Set<string>());
 
   // Check for active task on mount
@@ -215,12 +219,36 @@ export function AgentLiveCard({ issueId, agentName }: AgentLiveCardProps) {
   // Elapsed time
   useEffect(() => {
     if (!activeTask?.started_at && !activeTask?.dispatched_at) return;
-    const ref = activeTask.started_at ?? activeTask.dispatched_at!;
-    setElapsed(formatElapsed(ref));
-    const interval = setInterval(() => setElapsed(formatElapsed(ref)), 1000);
+    const startRef = activeTask.started_at ?? activeTask.dispatched_at!;
+    setElapsed(formatElapsed(startRef));
+    const interval = setInterval(() => setElapsed(formatElapsed(startRef)), 1000);
     return () => clearInterval(interval);
   }, [activeTask?.started_at, activeTask?.dispatched_at]);
 
+  // Sentinel pattern: detect when the card is scrolled past and becomes "stuck"
+  useEffect(() => {
+    const sentinel = sentinelRef.current;
+    const root = scrollContainerRef?.current;
+    if (!sentinel || !root || !activeTask) {
+      setIsStuck(false);
+      return;
+    }
+
+    const observer = new IntersectionObserver(
+      (entries) => {
+        if (entries[0]) setIsStuck(!entries[0].isIntersecting);
+      },
+      { root, threshold: 0, rootMargin: "-40px 0px 0px 0px" },
+    );
+
+    observer.observe(sentinel);
+    return () => observer.disconnect();
+  }, [scrollContainerRef, activeTask]);
+
+  const scrollToCard = useCallback(() => {
+    sentinelRef.current?.scrollIntoView({ behavior: "smooth", block: "center" });
+  }, []);
+
   // Auto-scroll
   useEffect(() => {
     if (autoScroll && scrollRef.current) {
@@ -248,67 +276,100 @@ export function AgentLiveCard({ issueId, agentName }: AgentLiveCardProps) {
   if (!activeTask) return null;
 
   const toolCount = items.filter((i) => i.type === "tool_use").length;
+  const name = (activeTask.agent_id ? getActorName("agent", activeTask.agent_id) : agentName) ?? "Agent";
 
   return (
-    <div className="rounded-lg border border-info/20 bg-info/5">
-      {/* Header */}
-      <div className="flex items-center gap-2 px-3 py-2">
-        <div className="flex items-center justify-center h-5 w-5 rounded-full bg-info/10 text-info shrink-0">
-          <Bot className="h-3 w-3" />
-        </div>
-        <div className="flex items-center gap-1.5 text-xs font-medium min-w-0">
-          <Loader2 className="h-3 w-3 animate-spin text-info shrink-0" />
-          <span className="truncate">{(activeTask?.agent_id ? getActorName("agent", activeTask.agent_id) : agentName) ?? "Agent"} is working</span>
-        </div>
-        <span className="ml-auto text-xs text-muted-foreground tabular-nums shrink-0">{elapsed}</span>
-        {toolCount > 0 && (
-          <span className="text-xs text-muted-foreground shrink-0">
-            {toolCount} tool {toolCount === 1 ? "call" : "calls"}
-          </span>
+    <>
+      {/* Sentinel — zero-height element that IntersectionObserver watches */}
+      <div ref={sentinelRef} className="mt-4 h-0 pointer-events-none" aria-hidden />
+
+      <div
+        className={cn(
+          "rounded-lg border transition-all duration-200",
+          isStuck
+            ? "sticky top-4 z-10 shadow-md border-brand/30 bg-brand/10 backdrop-blur-md"
+            : "border-info/20 bg-info/5",
         )}
-        <button
-          onClick={handleCancel}
-          disabled={cancelling}
-          className="flex items-center gap-1 rounded px-1.5 py-0.5 text-xs text-muted-foreground hover:text-destructive hover:bg-destructive/10 transition-colors disabled:opacity-50 shrink-0"
-          title="Stop agent"
-        >
-          {cancelling ? (
-            <Loader2 className="h-3 w-3 animate-spin" />
-          ) : (
-            <Square className="h-3 w-3" />
+      >
+        {/* Header */}
+        <div className="flex items-center gap-2 px-3 py-2">
+          <div className={cn(
+            "flex items-center justify-center h-5 w-5 rounded-full shrink-0",
+            isStuck ? "bg-brand/15 text-brand" : "bg-info/10 text-info",
+          )}>
+            <Bot className="h-3 w-3" />
+          </div>
+          <div className="flex items-center gap-1.5 text-xs font-medium min-w-0">
+            <Loader2 className={cn("h-3 w-3 animate-spin shrink-0", isStuck ? "text-brand" : "text-info")} />
+            <span className="truncate">{name} is working</span>
+          </div>
+          <span className="ml-auto text-xs text-muted-foreground tabular-nums shrink-0">{elapsed}</span>
+          {!isStuck && toolCount > 0 && (
+            <span className="text-xs text-muted-foreground shrink-0">
+              {toolCount} tool {toolCount === 1 ? "call" : "calls"}
+            </span>
           )}
-          <span>Stop</span>
-        </button>
-      </div>
-
-      {/* Timeline content */}
-      {items.length > 0 && (
-        <div
-          ref={scrollRef}
-          onScroll={handleScroll}
-          className="relative max-h-80 overflow-y-auto border-t border-info/10 px-3 py-2 space-y-0.5"
-        >
-          {items.map((item, idx) => (
-            <TimelineRow key={`${item.seq}-${idx}`} item={item} />
-          ))}
-
-          {!autoScroll && (
+          {isStuck ? (
             <button
-              onClick={() => {
-                if (scrollRef.current) {
-                  scrollRef.current.scrollTop = scrollRef.current.scrollHeight;
-                  setAutoScroll(true);
-                }
-              }}
-              className="sticky bottom-0 left-1/2 -translate-x-1/2 flex items-center gap-1 rounded-full bg-background border px-2 py-0.5 text-xs text-muted-foreground hover:text-foreground shadow-sm"
+              onClick={scrollToCard}
+              className="flex items-center gap-1 rounded px-1.5 py-0.5 text-xs text-muted-foreground hover:text-foreground transition-colors shrink-0"
+              title="Scroll to live card"
             >
-              <ArrowDown className="h-3 w-3" />
-              Latest
+              <ChevronUp className="h-3.5 w-3.5" />
+            </button>
+          ) : (
+            <button
+              onClick={handleCancel}
+              disabled={cancelling}
+              className="flex items-center gap-1 rounded px-1.5 py-0.5 text-xs text-muted-foreground hover:text-destructive hover:bg-destructive/10 transition-colors disabled:opacity-50 shrink-0"
+              title="Stop agent"
+            >
+              {cancelling ? (
+                <Loader2 className="h-3 w-3 animate-spin" />
+              ) : (
+                <Square className="h-3 w-3" />
+              )}
+              <span>Stop</span>
             </button>
           )}
         </div>
-      )}
-    </div>
+
+        {/* Timeline content — collapses when stuck */}
+        <div
+          className={cn(
+            "overflow-hidden transition-all duration-200",
+            isStuck ? "max-h-0 opacity-0" : "max-h-[20rem] opacity-100",
+          )}
+        >
+          {items.length > 0 && (
+            <div
+              ref={scrollRef}
+              onScroll={handleScroll}
+              className="relative max-h-80 overflow-y-auto border-t border-info/10 px-3 py-2 space-y-0.5"
+            >
+              {items.map((item, idx) => (
+                <TimelineRow key={`${item.seq}-${idx}`} item={item} />
+              ))}
+
+              {!autoScroll && (
+                <button
+                  onClick={() => {
+                    if (scrollRef.current) {
+                      scrollRef.current.scrollTop = scrollRef.current.scrollHeight;
+                      setAutoScroll(true);
+                    }
+                  }}
+                  className="sticky bottom-0 left-1/2 -translate-x-1/2 flex items-center gap-1 rounded-full bg-background border px-2 py-0.5 text-xs text-muted-foreground hover:text-foreground shadow-sm"
+                >
+                  <ArrowDown className="h-3 w-3" />
+                  Latest
+                </button>
+              )}
+            </div>
+          )}
+        </div>
+      </div>
+    </>
   );
 }
 
diff --git a/apps/web/features/issues/components/issue-detail.tsx b/apps/web/features/issues/components/issue-detail.tsx
index 4343a2ba..8b3687b7 100644
--- a/apps/web/features/issues/components/issue-detail.tsx
+++ b/apps/web/features/issues/components/issue-detail.tsx
@@ -771,12 +771,11 @@ export function IssueDetail({ issueId, onDelete, defaultSidebarOpen = true, layo
             </div>
 
             {/* Agent live output */}
-            <div className="mt-4">
-              <AgentLiveCard
-                issueId={id}
-                agentName={issue.assignee_type === "agent" && issue.assignee_id ? getActorName("agent", issue.assignee_id) : undefined}
-              />
-            </div>
+            <AgentLiveCard
+              issueId={id}
+              agentName={issue.assignee_type === "agent" && issue.assignee_id ? getActorName("agent", issue.assignee_id) : undefined}
+              scrollContainerRef={scrollContainerRef}
+            />
 
             {/* Agent execution history */}
             <div className="mt-3">