diff --git a/agents/gsd-roadmapper.md b/agents/gsd-roadmapper.md
index 9ba54e2d4..0b1f18a49 100644
--- a/agents/gsd-roadmapper.md
+++ b/agents/gsd-roadmapper.md
@@ -325,6 +325,35 @@ After roadmap creation, REQUIREMENTS.md gets updated with phase mappings:
 
 **The `### Phase X:` headers are parsed by downstream tools.** If you only write the summary checklist, phase lookups will fail.
 
+### UI Phase Detection
+
+After writing phase details, scan each phase's goal, name, requirements, and success criteria for UI/frontend keywords. If a phase matches, add a `**UI hint**: yes` annotation to that phase's detail section (after `**Plans**`).
+
+**Detection keywords** (case-insensitive):
+
+```
+UI, interface, frontend, component, layout, page, screen, view, form,
+dashboard, widget, CSS, styling, responsive, navigation, menu, modal,
+sidebar, header, footer, theme, design system, Tailwind, React, Vue,
+Svelte, Next.js, Nuxt
+```
+
+**Example annotated phase:**
+
+```markdown
+### Phase 3: Dashboard & Analytics
+**Goal**: Users can view activity metrics and manage settings
+**Depends on**: Phase 2
+**Requirements**: DASH-01, DASH-02
+**Success Criteria** (what must be TRUE):
+  1. User can view a dashboard with key metrics
+  2. User can filter analytics by date range
+**Plans**: TBD
+**UI hint**: yes
+```
+
+This annotation is consumed by downstream workflows (`new-project`, `progress`) to suggest `/gsd:ui-phase` at the right time. Phases without UI indicators omit the annotation entirely.
+
 ### 3. Progress Table
 
 ```markdown
diff --git a/get-shit-done/workflows/new-project.md b/get-shit-done/workflows/new-project.md
index 3ff69bb69..10dda7452 100644
--- a/get-shit-done/workflows/new-project.md
+++ b/get-shit-done/workflows/new-project.md
@@ -1131,6 +1131,37 @@ Exit skill and invoke SlashCommand("/gsd:discuss-phase 1 --auto")
 
 **If interactive mode:**
 
+Check if Phase 1 has UI indicators (look for `**UI hint**: yes` in Phase 1 detail section of ROADMAP.md):
+
+```bash
+PHASE1_SECTION=$(node "$HOME/.claude/get-shit-done/bin/gsd-tools.cjs" roadmap get-phase 1 2>/dev/null)
+PHASE1_HAS_UI=$(echo "$PHASE1_SECTION" | grep -qi "UI hint.*yes" && echo "true" || echo "false")
+```
+
+**If Phase 1 has UI (`PHASE1_HAS_UI` is `true`):**
+
+```
+───────────────────────────────────────────────────────────────
+
+## ▶ Next Up
+
+**Phase 1: [Phase Name]** — [Goal from ROADMAP.md]
+
+/gsd:discuss-phase 1 — gather context and clarify approach
+
+<sub>/clear first → fresh context window</sub>
+
+---
+
+**Also available:**
+- /gsd:ui-phase 1 — generate UI design contract (recommended for frontend phases)
+- /gsd:plan-phase 1 — skip discussion, plan directly
+
+───────────────────────────────────────────────────────────────
+```
+
+**If Phase 1 has no UI:**
+
 ```
 ───────────────────────────────────────────────────────────────
 
diff --git a/get-shit-done/workflows/progress.md b/get-shit-done/workflows/progress.md
index 58b7a8ca9..318811457 100644
--- a/get-shit-done/workflows/progress.md
+++ b/get-shit-done/workflows/progress.md
@@ -228,6 +228,13 @@ Read its `<objective>` section.
 
 Check if `{phase_num}-CONTEXT.md` exists in phase directory.
 
+Check if current phase has UI indicators:
+
+```bash
+PHASE_SECTION=$(node "$HOME/.claude/get-shit-done/bin/gsd-tools.cjs" roadmap get-phase "${CURRENT_PHASE}" 2>/dev/null)
+PHASE_HAS_UI=$(echo "$PHASE_SECTION" | grep -qi "UI hint.*yes" && echo "true" || echo "false")
+```
+
 **If CONTEXT.md exists:**
 
 ```
@@ -245,7 +252,30 @@ Check if `{phase_num}-CONTEXT.md` exists in phase directory.
 ---
 ```
 
-**If CONTEXT.md does NOT exist:**
+**If CONTEXT.md does NOT exist AND phase has UI (`PHASE_HAS_UI` is `true`):**
+
+```
+---
+
+## ▶ Next Up
+
+**Phase {N}: {Name}** — {Goal from ROADMAP.md}
+
+`/gsd:discuss-phase {phase}` — gather context and clarify approach
+
+<sub>`/clear` first → fresh context window</sub>
+
+---
+
+**Also available:**
+- `/gsd:ui-phase {phase}` — generate UI design contract (recommended for frontend phases)
+- `/gsd:plan-phase {phase}` — skip discussion, plan directly
+- `/gsd:list-phase-assumptions {phase}` — see Claude's assumptions
+
+---
+```
+
+**If CONTEXT.md does NOT exist AND phase has no UI:**
 
 ```
 ---
@@ -344,6 +374,40 @@ State: "Current phase is {X}. Milestone has {N} phases (highest: {Y})."
 
 Read ROADMAP.md to get the next phase's name and goal.
 
+Check if next phase has UI indicators:
+
+```bash
+NEXT_PHASE_SECTION=$(node "$HOME/.claude/get-shit-done/bin/gsd-tools.cjs" roadmap get-phase "$((Z+1))" 2>/dev/null)
+NEXT_HAS_UI=$(echo "$NEXT_PHASE_SECTION" | grep -qi "UI hint.*yes" && echo "true" || echo "false")
+```
+
+**If next phase has UI (`NEXT_HAS_UI` is `true`):**
+
+```
+---
+
+## ✓ Phase {Z} Complete
+
+## ▶ Next Up
+
+**Phase {Z+1}: {Name}** — {Goal from ROADMAP.md}
+
+`/gsd:discuss-phase {Z+1}` — gather context and clarify approach
+
+<sub>`/clear` first → fresh context window</sub>
+
+---
+
+**Also available:**
+- `/gsd:ui-phase {Z+1}` — generate UI design contract (recommended for frontend phases)
+- `/gsd:plan-phase {Z+1}` — skip discussion, plan directly
+- `/gsd:verify-work {Z}` — user acceptance test before continuing
+
+---
+```
+
+**If next phase has no UI:**
+
 ```
 ---