diff --git a/surfsense_web/components/assistant-ui/connector-popup/components/date-range-selector.tsx b/surfsense_web/components/assistant-ui/connector-popup/components/date-range-selector.tsx
index 48dc2a6c2..7490aa959 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/components/date-range-selector.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/components/date-range-selector.tsx
@@ -15,6 +15,7 @@ interface DateRangeSelectorProps {
 	onStartDateChange: (date: Date | undefined) => void;
 	onEndDateChange: (date: Date | undefined) => void;
 	allowFutureDates?: boolean; // Allow future dates for calendar connectors
+	lastIndexedAt?: string | null; // Last sync timestamp to show in default placeholder
 }
 
 export const DateRangeSelector: FC<DateRangeSelectorProps> = ({
@@ -23,7 +24,21 @@ export const DateRangeSelector: FC<DateRangeSelectorProps> = ({
 	onStartDateChange,
 	onEndDateChange,
 	allowFutureDates = false,
+	lastIndexedAt,
 }) => {
+	// Get the placeholder text for start date based on whether connector was previously indexed
+	const getStartDatePlaceholder = () => {
+		if (lastIndexedAt) {
+			const date = new Date(lastIndexedAt);
+			const currentYear = new Date().getFullYear();
+			const indexedYear = date.getFullYear();
+			// Show year only if different from current year
+			const formatStr = indexedYear === currentYear ? "MMM d, HH:mm" : "MMM d, yyyy HH:mm";
+			const formattedDate = format(date, formatStr);
+			return `Since (${formattedDate})`;
+		}
+		return "Default (1 year ago)";
+	};
 	const handleLast30Days = () => {
 		const today = new Date();
 		onStartDateChange(subDays(today, 30));
@@ -73,7 +88,7 @@ export const DateRangeSelector: FC<DateRangeSelectorProps> = ({
 								)}
 							>
 								<CalendarIcon className="mr-2 h-4 w-4" />
-								{startDate ? format(startDate, "PPP") : "Default (1 year ago)"}
+								{startDate ? format(startDate, "PPP") : getStartDatePlaceholder()}
 							</Button>
 						</PopoverTrigger>
 						<PopoverContent className="w-auto p-0 z-[100]" align="start">
diff --git a/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/connector-edit-view.tsx b/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/connector-edit-view.tsx
index 430aa927c..cfdebee60 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/connector-edit-view.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/connector-edit-view.tsx
@@ -227,6 +227,7 @@ export const ConnectorEditView: FC<ConnectorEditViewProps> = ({
 												connector.connector_type === "COMPOSIO_GOOGLE_CALENDAR_CONNECTOR" ||
 												connector.connector_type === "LUMA_CONNECTOR"
 											}
+											lastIndexedAt={connector.last_indexed_at}
 										/>
 									)}
 
diff --git a/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/indexing-configuration-view.tsx b/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/indexing-configuration-view.tsx
index 72069441a..b885f35da 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/indexing-configuration-view.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup/connector-configs/views/indexing-configuration-view.tsx
@@ -165,6 +165,7 @@ export const IndexingConfigurationView: FC<IndexingConfigurationViewProps> = ({
 												config.connectorType === "COMPOSIO_GOOGLE_CALENDAR_CONNECTOR" ||
 												config.connectorType === "LUMA_CONNECTOR"
 											}
+											lastIndexedAt={connector?.last_indexed_at}
 										/>
 									)}