diff --git a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
index 2d55f4d20..f5de0be7d 100644
--- a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
+++ b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
@@ -499,10 +499,14 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 			const empty = text.length === 0 && mentionedDocs.size === 0;
 			setIsEmpty(empty);
 
-			// Check for @ mentions
+			// Unified trigger scan: find the leftmost @ or / in the current word.
+			// Whichever trigger was typed first owns the token — the other character
+			// is treated as part of the query, not as a separate trigger.
 			const selection = window.getSelection();
 			let shouldTriggerMention = false;
 			let mentionQuery = "";
+			let shouldTriggerAction = false;
+			let actionQuery = "";
 
 			if (selection && selection.rangeCount > 0) {
 				const range = selection.getRangeAt(0);
@@ -512,63 +516,41 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 					const textContent = textNode.textContent || "";
 					const cursorPos = range.startOffset;
 
-					// Look for @ before cursor
-					let atIndex = -1;
+					let wordStart = 0;
 					for (let i = cursorPos - 1; i >= 0; i--) {
-						if (textContent[i] === "@") {
-							atIndex = i;
-							break;
-						}
-						// Stop if we hit a space (@ must be at word boundary)
 						if (textContent[i] === " " || textContent[i] === "\n") {
+							wordStart = i + 1;
 							break;
 						}
 					}
 
-					if (atIndex !== -1) {
-						const query = textContent.slice(atIndex + 1, cursorPos);
-						// Only trigger if query doesn't start with space
+					let triggerChar: "@" | "/" | null = null;
+					let triggerIndex = -1;
+					for (let i = wordStart; i < cursorPos; i++) {
+						if (textContent[i] === "@" || textContent[i] === "/") {
+							triggerChar = textContent[i] as "@" | "/";
+							triggerIndex = i;
+							break;
+						}
+					}
+
+					if (triggerChar === "@" && triggerIndex !== -1) {
+						const query = textContent.slice(triggerIndex + 1, cursorPos);
 						if (!query.startsWith(" ")) {
 							shouldTriggerMention = true;
 							mentionQuery = query;
 						}
-					}
-				}
-			}
-
-			// Check for / actions (same pattern as @)
-			let shouldTriggerAction = false;
-			let actionQuery = "";
-
-			if (!shouldTriggerMention && selection && selection.rangeCount > 0) {
-				const range = selection.getRangeAt(0);
-				const textNode = range.startContainer;
-
-				if (textNode.nodeType === Node.TEXT_NODE) {
-					const textContent = textNode.textContent || "";
-					const cursorPos = range.startOffset;
-
-					let slashIndex = -1;
-					for (let i = cursorPos - 1; i >= 0; i--) {
-						if (textContent[i] === "/") {
-							slashIndex = i;
-							break;
-						}
-						if (textContent[i] === " " || textContent[i] === "\n") {
-							break;
-						}
-					}
-
-					if (
-						slashIndex !== -1 &&
-						(slashIndex === 0 ||
-							textContent[slashIndex - 1] === " " ||
-							textContent[slashIndex - 1] === "\n")
-					) {
-						const query = textContent.slice(slashIndex + 1, cursorPos);
-						if (!query.startsWith(" ")) {
-							shouldTriggerAction = true;
-							actionQuery = query;
+					} else if (triggerChar === "/" && triggerIndex !== -1) {
+						if (
+							triggerIndex === 0 ||
+							textContent[triggerIndex - 1] === " " ||
+							textContent[triggerIndex - 1] === "\n"
+						) {
+							const query = textContent.slice(triggerIndex + 1, cursorPos);
+							if (!query.startsWith(" ")) {
+								shouldTriggerAction = true;
+								actionQuery = query;
+							}
 						}
 					}
 				}
diff --git a/surfsense_web/components/new-chat/document-mention-picker.tsx b/surfsense_web/components/new-chat/document-mention-picker.tsx
index 9c6521f31..a087463ba 100644
--- a/surfsense_web/components/new-chat/document-mention-picker.tsx
+++ b/surfsense_web/components/new-chat/document-mention-picker.tsx
@@ -394,12 +394,6 @@ export const DocumentMentionPicker = forwardRef<
 		[selectableDocuments, highlightedIndex, handleSelectDocument, onDone]
 	);
 
-	// Hide popup when there are no documents to display (regardless of fetch state)
-	// Search continues in background; popup reappears when results arrive
-	if (!actualLoading && actualDocuments.length === 0) {
-		return null;
-	}
-
 	return (
 		<div
 			className="fixed shadow-2xl rounded-lg border border-border dark:border-white/5 overflow-hidden bg-popover dark:bg-neutral-900 flex flex-col w-[280px] sm:w-[320px] select-none"
@@ -547,7 +541,11 @@ export const DocumentMentionPicker = forwardRef<
 							</div>
 						)}
 					</div>
-				) : null}
+				) : (
+					<div className="py-1 px-2">
+						<p className="px-3 py-2 text-xs text-muted-foreground">No matching documents</p>
+					</div>
+				)}
 			</div>
 		</div>
 	);
diff --git a/surfsense_web/components/new-chat/prompt-picker.tsx b/surfsense_web/components/new-chat/prompt-picker.tsx
index 3e6457b8c..d3166cad1 100644
--- a/surfsense_web/components/new-chat/prompt-picker.tsx
+++ b/surfsense_web/components/new-chat/prompt-picker.tsx
@@ -15,7 +15,7 @@ import {
 
 import { promptsAtom } from "@/atoms/prompts/prompts-query.atoms";
 import { userSettingsDialogAtom } from "@/atoms/settings/settings-dialog.atoms";
-import { Spinner } from "@/components/ui/spinner";
+import { Skeleton } from "@/components/ui/skeleton";
 import { cn } from "@/lib/utils";
 
 export interface PromptPickerRef {
@@ -60,13 +60,21 @@ export const PromptPicker = forwardRef<PromptPickerRef, PromptPickerProps>(funct
 		}
 	}
 
+	const createPromptIndex = filtered.length;
+	const totalItems = filtered.length + 1;
+
 	const handleSelect = useCallback(
 		(index: number) => {
+			if (index === createPromptIndex) {
+				onDone();
+				setUserSettingsDialog({ open: true, initialTab: "prompts" });
+				return;
+			}
 			const action = filtered[index];
 			if (!action) return;
 			onSelect({ name: action.name, prompt: action.prompt, mode: action.mode });
 		},
-		[filtered, onSelect]
+		[filtered, onSelect, createPromptIndex, onDone, setUserSettingsDialog]
 	);
 
 	useEffect(() => {
@@ -93,69 +101,104 @@ export const PromptPicker = forwardRef<PromptPickerRef, PromptPickerProps>(funct
 		() => ({
 			selectHighlighted: () => handleSelect(highlightedIndex),
 			moveUp: () => {
-				if (filtered.length === 0) return;
 				shouldScrollRef.current = true;
-				setHighlightedIndex((prev) => (prev > 0 ? prev - 1 : filtered.length - 1));
+				setHighlightedIndex((prev) => (prev > 0 ? prev - 1 : totalItems - 1));
 			},
 			moveDown: () => {
-				if (filtered.length === 0) return;
 				shouldScrollRef.current = true;
-				setHighlightedIndex((prev) => (prev < filtered.length - 1 ? prev + 1 : 0));
+				setHighlightedIndex((prev) => (prev < totalItems - 1 ? prev + 1 : 0));
 			},
 		}),
-		[filtered.length, highlightedIndex, handleSelect]
+		[totalItems, highlightedIndex, handleSelect]
 	);
 
 	return (
 		<div
-			className="w-64 rounded-lg border bg-popover shadow-lg overflow-hidden"
-			style={containerStyle}
+			className="fixed shadow-2xl rounded-lg border border-border dark:border-white/5 overflow-hidden bg-popover dark:bg-neutral-900 flex flex-col w-[280px] sm:w-[320px] select-none"
+			style={{
+				zIndex: 9999,
+				...containerStyle,
+			}}
 		>
-			<div ref={scrollContainerRef} className="max-h-48 overflow-y-auto py-1">
+			<div ref={scrollContainerRef} className="max-h-[180px] sm:max-h-[280px] overflow-y-auto">
 				{isLoading ? (
-					<div className="flex items-center justify-center py-3">
-						<Spinner className="size-4" />
+					<div className="py-1 px-2">
+						<div className="px-3 py-2">
+							<Skeleton className="h-[16px] w-24" />
+						</div>
+						{["a", "b", "c", "d", "e"].map((id, i) => (
+							<div
+								key={id}
+								className={cn(
+									"w-full flex items-center gap-2 px-3 py-2 text-left rounded-md",
+									i >= 3 && "hidden sm:flex"
+								)}
+							>
+								<span className="shrink-0">
+									<Skeleton className="h-4 w-4" />
+								</span>
+								<span className="flex-1 text-sm">
+									<Skeleton className="h-[20px]" style={{ width: `${60 + ((i * 7) % 30)}%` }} />
+								</span>
+							</div>
+						))}
 					</div>
 				) : isError ? (
-					<p className="px-3 py-2 text-xs text-destructive">Failed to load prompts</p>
+					<div className="py-1 px-2">
+						<p className="px-3 py-2 text-xs text-destructive">Failed to load prompts</p>
+					</div>
 				) : filtered.length === 0 ? (
-					<p className="px-3 py-2 text-xs text-muted-foreground">No matching prompts</p>
+					<div className="py-1 px-2">
+						<p className="px-3 py-2 text-xs text-muted-foreground">No matching prompts</p>
+					</div>
 				) : (
-					filtered.map((action, index) => (
+					<div className="py-1 px-2">
+						<div className="px-3 py-2 text-xs font-bold text-muted-foreground/55">
+							Saved Prompts
+						</div>
+						{filtered.map((action, index) => (
+							<button
+								key={action.id}
+								ref={(el) => {
+									if (el) itemRefs.current.set(index, el);
+									else itemRefs.current.delete(index);
+								}}
+								type="button"
+								onClick={() => handleSelect(index)}
+								onMouseEnter={() => setHighlightedIndex(index)}
+								className={cn(
+									"w-full flex items-center gap-2 px-3 py-2 text-left text-sm transition-colors rounded-md cursor-pointer",
+									index === highlightedIndex && "bg-accent"
+								)}
+							>
+								<span className="shrink-0 text-muted-foreground">
+									<Zap className="size-4" />
+								</span>
+								<span className="flex-1 text-sm truncate">{action.name}</span>
+							</button>
+						))}
+
+						<div className="mx-2 my-1 border-t border-border dark:border-white/5" />
 						<button
-							key={action.id}
 							ref={(el) => {
-								if (el) itemRefs.current.set(index, el);
-								else itemRefs.current.delete(index);
+								if (el) itemRefs.current.set(createPromptIndex, el);
+								else itemRefs.current.delete(createPromptIndex);
 							}}
 							type="button"
-							onClick={() => handleSelect(index)}
-							onMouseEnter={() => setHighlightedIndex(index)}
+							onClick={() => handleSelect(createPromptIndex)}
+							onMouseEnter={() => setHighlightedIndex(createPromptIndex)}
 							className={cn(
-								"flex w-full items-center gap-2 px-3 py-1.5 text-sm cursor-pointer",
-								index === highlightedIndex ? "bg-accent" : "hover:bg-accent/50"
+								"w-full flex items-center gap-2 px-3 py-2 text-left text-sm transition-colors rounded-md cursor-pointer text-muted-foreground",
+								highlightedIndex === createPromptIndex ? "bg-accent text-foreground" : "hover:text-foreground hover:bg-accent/50"
 							)}
 						>
-							<span className="text-muted-foreground">
-								<Zap className="size-3.5" />
+							<span className="shrink-0">
+								<Plus className="size-4" />
 							</span>
-							<span className="truncate">{action.name}</span>
+							<span>Create prompt</span>
 						</button>
-					))
+					</div>
 				)}
-
-				<div className="my-1 h-px bg-border mx-2" />
-				<button
-					type="button"
-					onClick={() => {
-						onDone();
-						setUserSettingsDialog({ open: true, initialTab: "prompts" });
-					}}
-					className="flex w-full items-center gap-2 px-3 py-1.5 text-sm text-muted-foreground hover:text-foreground hover:bg-accent/50 cursor-pointer"
-				>
-					<Plus className="size-3.5" />
-					<span>Create prompt</span>
-				</button>
 			</div>
 		</div>
 	);