diff --git a/apps/web/src/App.tsx b/apps/web/src/App.tsx
index f08446e..c94768d 100644
--- a/apps/web/src/App.tsx
+++ b/apps/web/src/App.tsx
@@ -2,7 +2,12 @@ import {
 	rollAllInitiativeUseCase,
 	rollInitiativeUseCase,
 } from "@initiative/application";
-import type { CombatantId, Creature, CreatureId } from "@initiative/domain";
+import {
+	type CombatantId,
+	type Creature,
+	type CreatureId,
+	isDomainError,
+} from "@initiative/domain";
 import {
 	useCallback,
 	useEffect,
@@ -109,6 +114,8 @@ export function App() {
 
 	const bulkImport = useBulkImport();
 
+	const [rollSkippedCount, setRollSkippedCount] = useState(0);
+
 	const [selectedCreatureId, setSelectedCreatureId] =
 		useState<CreatureId | null>(null);
 	const [bulkImportMode, setBulkImportMode] = useState(false);
@@ -158,7 +165,10 @@ export function App() {
 	);
 
 	const handleRollAllInitiative = useCallback(() => {
-		rollAllInitiativeUseCase(makeStore(), rollDice, getCreature);
+		const result = rollAllInitiativeUseCase(makeStore(), rollDice, getCreature);
+		if (!isDomainError(result) && result.skippedNoSource > 0) {
+			setRollSkippedCount(result.skippedNoSource);
+		}
 	}, [makeStore, getCreature]);
 
 	const handleViewStatBlock = useCallback((result: SearchResult) => {
@@ -252,7 +262,10 @@ export function App() {
 	}, [encounter.activeIndex, encounter.combatants, isLoaded]);
 
 	const isEmpty = encounter.combatants.length === 0;
-	const showRollAllInitiative = encounter.combatants.some(
+	const hasCreatureCombatants = encounter.combatants.some(
+		(c) => c.creatureId != null,
+	);
+	const canRollAllInitiative = encounter.combatants.some(
 		(c) => c.creatureId != null && c.initiative == null,
 	);
 
@@ -293,7 +306,8 @@ export function App() {
 								onAddFromPlayerCharacter={addFromPlayerCharacter}
 								onManagePlayers={() => setManagementOpen(true)}
 								onRollAllInitiative={handleRollAllInitiative}
-								showRollAllInitiative={showRollAllInitiative}
+								showRollAllInitiative={hasCreatureCombatants}
+								rollAllInitiativeDisabled={!canRollAllInitiative}
 								onOpenSourceManager={handleOpenSourceManager}
 								autoFocus
 							/>
@@ -349,7 +363,8 @@ export function App() {
 								onAddFromPlayerCharacter={addFromPlayerCharacter}
 								onManagePlayers={() => setManagementOpen(true)}
 								onRollAllInitiative={handleRollAllInitiative}
-								showRollAllInitiative={showRollAllInitiative}
+								showRollAllInitiative={hasCreatureCombatants}
+								rollAllInitiativeDisabled={!canRollAllInitiative}
 								onOpenSourceManager={handleOpenSourceManager}
 							/>
 						</div>
@@ -427,6 +442,14 @@ export function App() {
 				/>
 			)}
 
+			{rollSkippedCount > 0 && (
+				<Toast
+					message={`${rollSkippedCount} skipped — bestiary source not loaded`}
+					onDismiss={() => setRollSkippedCount(0)}
+					autoDismissMs={4000}
+				/>
+			)}
+
 			<CreatePlayerModal
 				open={createPlayerOpen}
 				onClose={() => {
diff --git a/apps/web/src/components/action-bar.tsx b/apps/web/src/components/action-bar.tsx
index c5773a9..41c9416 100644
--- a/apps/web/src/components/action-bar.tsx
+++ b/apps/web/src/components/action-bar.tsx
@@ -40,6 +40,7 @@ interface ActionBarProps {
 	onManagePlayers?: () => void;
 	onRollAllInitiative?: () => void;
 	showRollAllInitiative?: boolean;
+	rollAllInitiativeDisabled?: boolean;
 	onOpenSourceManager?: () => void;
 	autoFocus?: boolean;
 }
@@ -262,6 +263,7 @@ export function ActionBar({
 	onManagePlayers,
 	onRollAllInitiative,
 	showRollAllInitiative,
+	rollAllInitiativeDisabled,
 	onOpenSourceManager,
 	autoFocus,
 }: ActionBarProps) {
@@ -575,6 +577,7 @@ export function ActionBar({
 						variant="ghost"
 						className="text-muted-foreground hover:text-hover-action"
 						onClick={onRollAllInitiative}
+						disabled={rollAllInitiativeDisabled}
 						title="Roll all initiative"
 						aria-label="Roll all initiative"
 					>
diff --git a/apps/web/src/components/toast.tsx b/apps/web/src/components/toast.tsx
index dd248fd..39b4985 100644
--- a/apps/web/src/components/toast.tsx
+++ b/apps/web/src/components/toast.tsx
@@ -23,7 +23,7 @@ export function Toast({
 	}, [autoDismissMs, onDismiss]);
 
 	return createPortal(
-		<div className="fixed bottom-4 left-1/2 z-50 -translate-x-1/2">
+		<div className="fixed bottom-4 left-4 z-50">
 			<div className="flex items-center gap-3 rounded-lg border border-border bg-card px-4 py-3 shadow-lg">
 				<span className="text-sm text-foreground">{message}</span>
 				{progress !== undefined && (
diff --git a/packages/application/src/index.ts b/packages/application/src/index.ts
index 895dfef..77ae634 100644
--- a/packages/application/src/index.ts
+++ b/packages/application/src/index.ts
@@ -13,7 +13,10 @@ export type {
 } from "./ports.js";
 export { removeCombatantUseCase } from "./remove-combatant-use-case.js";
 export { retreatTurnUseCase } from "./retreat-turn-use-case.js";
-export { rollAllInitiativeUseCase } from "./roll-all-initiative-use-case.js";
+export {
+	type RollAllResult,
+	rollAllInitiativeUseCase,
+} from "./roll-all-initiative-use-case.js";
 export { rollInitiativeUseCase } from "./roll-initiative-use-case.js";
 export { setAcUseCase } from "./set-ac-use-case.js";
 export { setHpUseCase } from "./set-hp-use-case.js";
diff --git a/packages/application/src/roll-all-initiative-use-case.ts b/packages/application/src/roll-all-initiative-use-case.ts
index a0c9e3a..b3fd646 100644
--- a/packages/application/src/roll-all-initiative-use-case.ts
+++ b/packages/application/src/roll-all-initiative-use-case.ts
@@ -10,20 +10,29 @@ import {
 } from "@initiative/domain";
 import type { EncounterStore } from "./ports.js";
 
+export interface RollAllResult {
+	events: DomainEvent[];
+	skippedNoSource: number;
+}
+
 export function rollAllInitiativeUseCase(
 	store: EncounterStore,
 	rollDice: () => number,
 	getCreature: (id: CreatureId) => Creature | undefined,
-): DomainEvent[] | DomainError {
+): RollAllResult | DomainError {
 	let encounter = store.get();
 	const allEvents: DomainEvent[] = [];
+	let skippedNoSource = 0;
 
 	for (const combatant of encounter.combatants) {
 		if (!combatant.creatureId) continue;
 		if (combatant.initiative !== undefined) continue;
 
 		const creature = getCreature(combatant.creatureId);
-		if (!creature) continue;
+		if (!creature) {
+			skippedNoSource++;
+			continue;
+		}
 
 		const { modifier } = calculateInitiative({
 			dexScore: creature.abilities.dex,
@@ -47,5 +56,5 @@ export function rollAllInitiativeUseCase(
 	}
 
 	store.save(encounter);
-	return allEvents;
+	return { events: allEvents, skippedNoSource };
 }