backend/app/core/config.py

@@ -111,14 +111,16 @@ class Settings(BaseSettings):
     GOOGLE_AI_API_KEY: Optional[str] = None
     AI_MODEL_GEMINI: str = "gemini-2.5-flash"
     AI_MODEL_ANTHROPIC: str = "claude-sonnet-4-6"
-    # 15s is generous for the click-path; Claude usually returns a 500-token
-    # diagnostic in 4-8s but tail latency on the assessment prompt has hit
-    # 12-14s in the field. Going below this leaves too many escalations with
-    # the "Assessment unavailable — model didn't respond in time" placeholder
-    # the senior sees on the magic-moment screen. Real fix is async generation
-    # (kick off, persist when done, surface "still computing" with refresh) —
-    # that's a follow-up; bumping the bound keeps the wedge demo coherent.
-    ESCALATION_AI_ASSESSMENT_TIMEOUT_SECONDS: int = 15
+    # Bound for the diagnostic assessment Sonnet call. Generation runs in a
+    # FastAPI BackgroundTask (commit e8ba74e), so this no longer blocks the
+    # senior's click — only how long we wait before publishing
+    # `handoff_assessment_ready` with has_assessment=false. 15s was hitting
+    # tail latency on Sonnet (timeout 03:57:35 in field testing 2026-04-29),
+    # leaving the magic-moment placeholder permanent. 45s is the right
+    # ceiling: well above Sonnet p99 for a 500-token output, far enough
+    # below "the senior gives up watching" that we still surface SOMETHING
+    # on persistent slowness.
+    ESCALATION_AI_ASSESSMENT_TIMEOUT_SECONDS: int = 45
 
     # Model tier routing — maps action types to model tiers
     AI_MODEL_TIERS: dict[str, str] = {

frontend/src/components/assistant/ConcludeSessionModal.tsx

@@ -348,6 +348,15 @@ export function ConcludeSessionModal({
                 <textarea
                   value={notes}
                   onChange={e => setNotes(e.target.value)}
+                  onKeyDown={e => {
+                    // Enter submits, Shift+Enter inserts newline — same
+                    // convention as the chat composer. Engineers write
+                    // short reasons here; multi-line is rare.
+                    if (e.key === 'Enter' && !e.shiftKey && !generating) {
+                      e.preventDefault()
+                      handleGenerate()
+                    }
+                  }}
                   placeholder={
                     outcome === 'resolved'
                       ? 'Any additional context about the resolution...'

frontend/src/components/common/RichTextInput.tsx

@@ -13,6 +13,11 @@ interface RichTextInputProps {
   rows?: number
   className?: string
   disabled?: boolean
+  // Enter-to-submit, matching the chat-input convention used elsewhere in
+  // the app: plain Enter calls onSubmit; Shift+Enter inserts a newline.
+  // Parents that want the legacy "Enter = newline only" behavior just
+  // omit this prop.
+  onSubmit?: () => void
 }
 
 export function RichTextInput({
@@ -24,6 +29,7 @@ export function RichTextInput({
   rows = 3,
   className,
   disabled,
+  onSubmit,
 }: RichTextInputProps) {
   const [pendingUploads, setPendingUploads] = useState<PendingUpload[]>([])
   const [isDragOver, setIsDragOver] = useState(false)
@@ -229,6 +235,12 @@ export function RichTextInput({
         onPaste={handlePaste}
         onFocus={() => setIsFocused(true)}
         onBlur={() => setIsFocused(false)}
+        onKeyDown={(e) => {
+          if (e.key === 'Enter' && !e.shiftKey && onSubmit) {
+            e.preventDefault()
+            onSubmit()
+          }
+        }}
         placeholder={placeholder}
         rows={rows}
         disabled={disabled}

frontend/src/components/dashboard/PendingEscalations.tsx

@@ -1,12 +1,16 @@
 import { useState, useEffect } from 'react'
 import { Link, useNavigate } from 'react-router-dom'
-import { AlertTriangle } from 'lucide-react'
+import { AlertTriangle, ChevronDown, ChevronRight, Hash } from 'lucide-react'
 import { aiSessionsApi } from '@/api/aiSessions'
 import type { AISessionSummary } from '@/types/ai-session'
 import { timeAgo } from '@/lib/timeAgo'
+import { cn } from '@/lib/utils'
 
 export function PendingEscalations() {
   const [escalations, setEscalations] = useState<AISessionSummary[]>([])
+  // Single expansion at a time — keeps the dashboard compact even when
+  // multiple escalations are pending. Click a row again to collapse.
+  const [expandedId, setExpandedId] = useState<string | null>(null)
   const navigate = useNavigate()
 
   useEffect(() => {
@@ -43,35 +47,107 @@ export function PendingEscalations() {
         </Link>
       </div>
       <div>
-        {escalations.slice(0, 3).map((esc, i) => (
-          <div
-            key={esc.id}
-            className="flex items-center gap-3 px-5 py-3"
-            style={{
-              borderBottom: i < Math.min(escalations.length, 3) - 1
-                ? '1px solid var(--color-border-default)'
-                : undefined,
-            }}
-          >
-            <span className="h-2 w-2 shrink-0 rounded-full bg-amber-400 animate-pulse" />
-            <div className="flex-1 min-w-0">
-              <div className="text-sm text-foreground truncate">
-                {esc.problem_summary || 'Escalated session'}
-              </div>
-              <div className="text-[0.6875rem] text-muted-foreground">
-                {esc.problem_domain || 'General'}
-                <span className="mx-1.5 text-[var(--text-dimmed)]">&middot;</span>
-                <span className="font-sans text-xs">{timeAgo(esc.created_at)}</span>
-              </div>
-            </div>
-            <button
-              onClick={() => navigate(`/pilot/${esc.id}?pickup=true`)}
-              className="shrink-0 rounded-lg border border-amber-400/30 bg-amber-400/10 px-3 py-1 text-[0.6875rem] font-medium text-amber-400 hover:bg-amber-400/20 transition-colors"
+        {escalations.slice(0, 3).map((esc, i) => {
+          const isExpanded = expandedId === esc.id
+          const isLast = i >= Math.min(escalations.length, 3) - 1
+          return (
+            <div
+              key={esc.id}
+              style={{
+                borderBottom: !isLast
+                  ? '1px solid var(--color-border-default)'
+                  : undefined,
+              }}
             >
-              Pick up
-            </button>
-          </div>
-        ))}
+              <button
+                type="button"
+                onClick={() => setExpandedId(isExpanded ? null : esc.id)}
+                aria-expanded={isExpanded}
+                className="w-full flex items-center gap-3 px-5 py-3 text-left hover:bg-elevated/30 transition-colors"
+              >
+                <span className="h-2 w-2 shrink-0 rounded-full bg-amber-400 animate-pulse" />
+                {isExpanded ? (
+                  <ChevronDown size={12} className="shrink-0 text-muted-foreground" />
+                ) : (
+                  <ChevronRight size={12} className="shrink-0 text-muted-foreground" />
+                )}
+                <div className="flex-1 min-w-0">
+                  <div className="text-sm text-foreground truncate">
+                    {esc.problem_summary || 'Escalated session'}
+                  </div>
+                  <div className="text-[0.6875rem] text-muted-foreground">
+                    {esc.problem_domain || 'General'}
+                    <span className="mx-1.5 text-[var(--text-dimmed)]">&middot;</span>
+                    <span className="font-sans text-xs">{timeAgo(esc.created_at)}</span>
+                    {esc.psa_ticket_id && (
+                      <>
+                        <span className="mx-1.5 text-[var(--text-dimmed)]">&middot;</span>
+                        <span className="inline-flex items-center gap-0.5 font-mono text-[0.625rem] text-accent-text">
+                          <Hash size={9} />
+                          {esc.psa_ticket_id}
+                        </span>
+                      </>
+                    )}
+                  </div>
+                </div>
+                <span
+                  onClick={(e) => {
+                    e.stopPropagation()
+                    navigate(`/pilot/${esc.id}?pickup=true`)
+                  }}
+                  role="button"
+                  tabIndex={0}
+                  onKeyDown={(e) => {
+                    if (e.key === 'Enter' || e.key === ' ') {
+                      e.preventDefault()
+                      e.stopPropagation()
+                      navigate(`/pilot/${esc.id}?pickup=true`)
+                    }
+                  }}
+                  className="shrink-0 rounded-lg border border-amber-400/30 bg-amber-400/10 px-3 py-1 text-[0.6875rem] font-medium text-amber-400 hover:bg-amber-400/20 transition-colors cursor-pointer"
+                >
+                  Pick up
+                </span>
+              </button>
+
+              {isExpanded && (
+                <div
+                  className={cn(
+                    'px-5 pb-3 pl-12 space-y-2 text-xs animate-fade-in'
+                  )}
+                >
+                  {esc.escalation_reason && (
+                    <div>
+                      <p className="font-sans text-[0.5625rem] uppercase tracking-wider text-muted-foreground mb-0.5">
+                        Why escalated
+                      </p>
+                      <p className="text-foreground whitespace-pre-wrap leading-snug">
+                        {esc.escalation_reason}
+                      </p>
+                    </div>
+                  )}
+                  <div className="flex flex-wrap gap-x-3 gap-y-1 text-muted-foreground">
+                    <span>
+                      <span className="font-medium text-foreground">{esc.step_count}</span>{' '}
+                      diagnostic {esc.step_count === 1 ? 'step' : 'steps'} on record
+                    </span>
+                    {esc.confidence_tier && (
+                      <span className="font-sans uppercase tracking-wider text-[0.5625rem]">
+                        Confidence: {esc.confidence_tier}
+                      </span>
+                    )}
+                  </div>
+                  {!esc.escalation_reason && (
+                    <p className="italic text-muted-foreground">
+                      No reason note from the original engineer. Pick up to see the full session
+                      context and AI assessment.
+                    </p>
+                  )}
+                </div>
+              )}
+            </div>
+          )
+        })}
       </div>
     </div>
   )

frontend/src/components/flowpilot/EscalateModal.tsx

@@ -53,6 +53,7 @@ export function EscalateModal({ open, onClose, onEscalate, isProcessing, hasPsaT
             sessionId={sessionId}
             placeholder="e.g. I've exhausted all networking diagnostics and suspect this is a firewall policy issue that requires senior admin access..."
             rows={4}
+            onSubmit={handleSubmit}
           />
           <p className="mt-1 text-[0.625rem] text-text-muted">
             Minimum 5 characters. This will be shown to the engineer who picks up.

frontend/src/pages/AssistantChatPage.tsx

@@ -256,6 +256,14 @@ export default function AssistantChatPage() {
   // Tracks the most recently requested active chat ID so in-flight selectChat
   // calls that complete after the user switches chats don't clobber new state.
   const currentChatRef = useRef<string | null>(activeChatId)
+  // Tracks which URL chatIds we've already loaded via selectChat in this
+  // page lifecycle. Replaces the old `urlSessionId === activeChatId` gate,
+  // which was buggy after commit 8914391 made activeChatId initialize from
+  // urlSessionId — they MATCH on mount, so the gate bailed and selectChat
+  // never fired for fresh entries (notably the bell-icon → ?pickup=true
+  // path: post-claim the chat surface had no messages and the senior
+  // landed on a blank pane).
+  const loadedChatIdsRef = useRef<Set<string>>(new Set())
 
   // Persist active chat ID to sessionStorage
   useEffect(() => {
@@ -275,9 +283,17 @@ export default function AssistantChatPage() {
   // own the session and the regular chat surface would race against the
   // claim flow. Once magicState is 'dismissed' (post-claim, or no handoff
   // found at all), this effect re-fires and selectChat runs.
+  //
+  // The dedupe is on a "have we loaded this URL session yet" ref instead
+  // of comparing to activeChatId — activeChatId now initializes from
+  // urlSessionId, so the old comparison short-circuited fresh mounts and
+  // selectChat never fired. The ref clears nothing on its own; if you
+  // need to force a reload, call selectChat directly.
   useEffect(() => {
-    if (!urlSessionId || urlSessionId === activeChatId) return
+    if (!urlSessionId) return
     if (magicState === 'loading' || magicState === 'visible') return
+    if (loadedChatIdsRef.current.has(urlSessionId)) return
+    loadedChatIdsRef.current.add(urlSessionId)
     selectChat(urlSessionId)
   }, [urlSessionId, magicState]) // eslint-disable-line react-hooks/exhaustive-deps
 
@@ -324,6 +340,14 @@ export default function AssistantChatPage() {
       // as chat history.
       setSearchParams({})
       setMagicState('dismissed')
+      // Refresh the sidebar list. Pre-claim the session was invisible to
+      // listSessions because escalated_to_id was null (junior didn't
+      // specify a target on /escalate). Post-claim claim_session sets
+      // escalated_to_id = teamadmin.id, so the session is now in scope.
+      // Without this re-fetch the senior lands on a session with no
+      // sidebar entry — looks like the page navigated to a different
+      // session.
+      void loadChats()
     } catch (e: unknown) {
       // Race-condition path (locked design): the loser of the simultaneous
       // Pick Up gets a 409 with structured detail so we can name the