diff --git a/surfsense_web/components/assistant-ui/connector-popup.tsx b/surfsense_web/components/assistant-ui/connector-popup.tsx
index a955e3972..8fb1e7652 100644
--- a/surfsense_web/components/assistant-ui/connector-popup.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup.tsx
@@ -189,7 +189,7 @@ export const ConnectorIndicator: FC = () => {
 				)}
 			</TooltipIconButton>
 
-			<DialogContent className="max-w-3xl w-[95vw] sm:w-full h-[90vh] sm:h-[85vh] flex flex-col p-0 gap-0 overflow-hidden border border-border bg-muted text-foreground [&>button]:right-6 sm:[&>button]:right-12 [&>button]:top-8 sm:[&>button]:top-10 [&>button]:opacity-80 hover:[&>button]:opacity-100 [&>button_svg]:size-5">
+			<DialogContent className="max-w-3xl w-[95vw] sm:w-full h-[75vh] sm:h-[85vh] flex flex-col p-0 gap-0 overflow-hidden border border-border bg-muted text-foreground [&>button]:right-4 sm:[&>button]:right-12 [&>button]:top-6 sm:[&>button]:top-10 [&>button]:opacity-80 hover:[&>button]:opacity-100 [&>button_svg]:size-5">
 				{/* YouTube Crawler View - shown when adding YouTube videos */}
 				{isYouTubeView && searchSpaceId ? (
 					<YouTubeCrawlerView searchSpaceId={searchSpaceId} onBack={handleBackFromYouTube} />
@@ -272,7 +272,7 @@ export const ConnectorIndicator: FC = () => {
 						{/* Content */}
 						<div className="flex-1 min-h-0 relative overflow-hidden">
 							<div className="h-full overflow-y-auto" onScroll={handleScroll}>
-								<div className="px-6 sm:px-12 py-6 sm:py-8 pb-16 sm:pb-16">
+								<div className="px-4 sm:px-12 py-4 sm:py-8 pb-12 sm:pb-16">
 									<TabsContent value="all" className="m-0">
 										<AllConnectorsTab
 											searchQuery={searchQuery}
diff --git a/surfsense_web/components/assistant-ui/connector-popup/components/connector-card.tsx b/surfsense_web/components/assistant-ui/connector-popup/components/connector-card.tsx
index 8cc36fd8e..da0b5b875 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/components/connector-card.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/components/connector-card.tsx
@@ -1,7 +1,13 @@
 "use client";
 
 import { IconBrandYoutube } from "@tabler/icons-react";
-import { format } from "date-fns";
+import {
+	differenceInDays,
+	differenceInMinutes,
+	format,
+	isToday,
+	isYesterday,
+} from "date-fns";
 import { FileText, Loader2 } from "lucide-react";
 import type { FC } from "react";
 import { Button } from "@/components/ui/button";
@@ -49,6 +55,45 @@ function formatDocumentCount(count: number | undefined): string {
 	return `${m.replace(/\.0$/, "")}M docs`;
 }
 
+/**
+ * Format last indexed date with contextual messages
+ * Examples: "Just now", "10 minutes ago", "Today at 2:30 PM", "Yesterday at 3:45 PM", "3 days ago", "Jan 15, 2026"
+ */
+function formatLastIndexedDate(dateString: string): string {
+	const date = new Date(dateString);
+	const now = new Date();
+	const minutesAgo = differenceInMinutes(now, date);
+	const daysAgo = differenceInDays(now, date);
+
+	// Just now (within last minute)
+	if (minutesAgo < 1) {
+		return "Just now";
+	}
+
+	// X minutes ago (less than 1 hour)
+	if (minutesAgo < 60) {
+		return `${minutesAgo} ${minutesAgo === 1 ? "minute" : "minutes"} ago`;
+	}
+
+	// Today at [time]
+	if (isToday(date)) {
+		return `Today at ${format(date, "h:mm a")}`;
+	}
+
+	// Yesterday at [time]
+	if (isYesterday(date)) {
+		return `Yesterday at ${format(date, "h:mm a")}`;
+	}
+
+	// X days ago (less than 7 days)
+	if (daysAgo < 7) {
+		return `${daysAgo} ${daysAgo === 1 ? "day" : "days"} ago`;
+	}
+
+	// Full date for older entries
+	return format(date, "MMM d, yyyy");
+}
+
 export const ConnectorCard: FC<ConnectorCardProps> = ({
 	id,
 	title,
@@ -86,13 +131,13 @@ export const ConnectorCard: FC<ConnectorCardProps> = ({
 			// Show last indexed date for connected connectors
 			if (lastIndexedAt) {
 				return (
-					<span className="whitespace-nowrap">
-						Last indexed: {format(new Date(lastIndexedAt), "MMM d, yyyy")}
+					<span className="whitespace-nowrap text-[10px]">
+						Last indexed: {formatLastIndexedDate(lastIndexedAt)}
 					</span>
 				);
 			}
 			// Fallback for connected but never indexed
-			return <span className="whitespace-nowrap">Never indexed</span>;
+			return <span className="whitespace-nowrap text-[10px]">Never indexed</span>;
 		}
 
 		return description;
@@ -113,9 +158,9 @@ export const ConnectorCard: FC<ConnectorCardProps> = ({
 				<div className="flex items-center gap-2">
 					<span className="text-[14px] font-semibold leading-tight">{title}</span>
 				</div>
-				<div className="text-[11px] text-muted-foreground mt-1">{getStatusContent()}</div>
+				<div className="text-[10px] text-muted-foreground mt-1">{getStatusContent()}</div>
 				{isConnected && documentCount !== undefined && (
-					<p className="text-[11px] text-muted-foreground mt-0.5">
+					<p className="text-[10px] text-muted-foreground mt-0.5">
 						{formatDocumentCount(documentCount)}
 					</p>
 				)}
diff --git a/surfsense_web/components/assistant-ui/connector-popup/components/connector-dialog-header.tsx b/surfsense_web/components/assistant-ui/connector-popup/components/connector-dialog-header.tsx
index a18c79a1f..f1a06de81 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/components/connector-dialog-header.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/components/connector-dialog-header.tsx
@@ -24,20 +24,20 @@ export const ConnectorDialogHeader: FC<ConnectorDialogHeaderProps> = ({
 	return (
 		<div
 			className={cn(
-				"flex-shrink-0 px-6 sm:px-12 pt-8 sm:pt-10 transition-shadow duration-200 relative z-10",
+				"flex-shrink-0 px-4 sm:px-12 pt-5 sm:pt-10 transition-shadow duration-200 relative z-10",
 				isScrolled && "shadow-xl bg-muted/50 backdrop-blur-md"
 			)}
 		>
 			<DialogHeader>
-				<DialogTitle className="text-2xl sm:text-3xl font-semibold tracking-tight">
+				<DialogTitle className="text-xl sm:text-3xl font-semibold tracking-tight">
 					Connectors
 				</DialogTitle>
-				<DialogDescription className="text-sm sm:text-base text-muted-foreground/80 mt-1 sm:mt-1.5">
+				<DialogDescription className="text-xs sm:text-base text-muted-foreground/80 mt-1 sm:mt-1.5">
 					Search across all your apps and data in one place.
 				</DialogDescription>
 			</DialogHeader>
 
-			<div className="flex flex-col-reverse sm:flex-row sm:items-end justify-between gap-6 sm:gap-8 mt-6 sm:mt-8 border-b border-border/80 dark:border-white/5">
+			<div className="flex flex-col-reverse sm:flex-row sm:items-end justify-between gap-4 sm:gap-8 mt-4 sm:mt-8 border-b border-border/80 dark:border-white/5">
 				<TabsList className="bg-transparent p-0 gap-4 sm:gap-8 h-auto w-full sm:w-auto justify-center sm:justify-start">
 					<TabsTrigger
 						value="all"
diff --git a/surfsense_web/components/assistant-ui/connector-popup/tabs/active-connectors-tab.tsx b/surfsense_web/components/assistant-ui/connector-popup/tabs/active-connectors-tab.tsx
index c28aaca52..12e0d4472 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/tabs/active-connectors-tab.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/tabs/active-connectors-tab.tsx
@@ -1,6 +1,12 @@
 "use client";
 
-import { format } from "date-fns";
+import {
+	differenceInDays,
+	differenceInMinutes,
+	format,
+	isToday,
+	isYesterday,
+} from "date-fns";
 import { ArrowRight, Cable, Loader2 } from "lucide-react";
 import { useRouter } from "next/navigation";
 import type { FC } from "react";
@@ -64,6 +70,42 @@ export const ActiveConnectorsTab: FC<ActiveConnectorsTabProps> = ({
 		return `${m.replace(/\.0$/, "")}M docs`;
 	};
 
+	// Format last indexed date with contextual messages
+	const formatLastIndexedDate = (dateString: string): string => {
+		const date = new Date(dateString);
+		const now = new Date();
+		const minutesAgo = differenceInMinutes(now, date);
+		const daysAgo = differenceInDays(now, date);
+
+		// Just now (within last minute)
+		if (minutesAgo < 1) {
+			return "Just now";
+		}
+
+		// X minutes ago (less than 1 hour)
+		if (minutesAgo < 60) {
+			return `${minutesAgo} ${minutesAgo === 1 ? "minute" : "minutes"} ago`;
+		}
+
+		// Today at [time]
+		if (isToday(date)) {
+			return `Today at ${format(date, "h:mm a")}`;
+		}
+
+		// Yesterday at [time]
+		if (isYesterday(date)) {
+			return `Yesterday at ${format(date, "h:mm a")}`;
+		}
+
+		// X days ago (less than 7 days)
+		if (daysAgo < 7) {
+			return `${daysAgo} ${daysAgo === 1 ? "day" : "days"} ago`;
+		}
+
+		// Full date for older entries
+		return format(date, "MMM d, yyyy");
+	};
+
 	// Document types that should be shown as cards (not from connectors)
 	// These are: EXTENSION (browser extension), FILE (uploaded files), NOTE (editor notes),
 	// YOUTUBE_VIDEO (YouTube videos), and CRAWLED_URL (web pages - shown separately even though it can come from WEBCRAWLER_CONNECTOR)
@@ -148,13 +190,13 @@ export const ActiveConnectorsTab: FC<ActiveConnectorsTabProps> = ({
 														)}
 													</p>
 												) : (
-													<p className="text-[11px] text-muted-foreground mt-1">
+													<p className="text-[10px] text-muted-foreground mt-1 whitespace-nowrap">
 														{connector.last_indexed_at
-															? `Last indexed: ${format(new Date(connector.last_indexed_at), "MMM d, yyyy")}`
+															? `Last indexed: ${formatLastIndexedDate(connector.last_indexed_at)}`
 															: "Never indexed"}
 													</p>
 												)}
-												<p className="text-[11px] text-muted-foreground mt-0.5">
+												<p className="text-[10px] text-muted-foreground mt-0.5">
 													{formatDocumentCount(documentCount)}
 												</p>
 											</div>