diff --git a/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx b/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
index 1d7416837..b68f335b4 100644
--- a/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
+++ b/surfsense_web/components/hitl-edit-panel/hitl-edit-panel.tsx
@@ -1,19 +1,22 @@
 "use client";
 
 import { TagInput, type Tag as TagType } from "emblor";
+import { format } from "date-fns";
 import { useAtomValue, useSetAtom } from "jotai";
-import { XIcon } from "lucide-react";
-import { useCallback, useEffect, useRef, useState } from "react";
+import { CalendarIcon, XIcon } from "lucide-react";
+import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import {
 	closeHitlEditPanelAtom,
 	hitlEditPanelAtom,
 } from "@/atoms/chat/hitl-edit-panel.atom";
 import type { ExtraField } from "@/atoms/chat/hitl-edit-panel.atom";
+import { Calendar } from "@/components/ui/calendar";
 import { PlateEditor } from "@/components/editor/plate-editor";
 import { Button } from "@/components/ui/button";
 import { Drawer, DrawerContent, DrawerHandle, DrawerTitle } from "@/components/ui/drawer";
 import { Input } from "@/components/ui/input";
 import { Label } from "@/components/ui/label";
+import { Popover, PopoverContent, PopoverTrigger } from "@/components/ui/popover";
 import { Textarea } from "@/components/ui/textarea";
 import { useMediaQuery } from "@/hooks/use-media-query";
 
@@ -44,14 +47,16 @@ function EmailsTagField({
 	const [tags, setTags] = useState<TagType[]>(() => parseEmailsToTags(value));
 	const [activeTagIndex, setActiveTagIndex] = useState<number | null>(null);
 	const isInitialMount = useRef(true);
+	const onChangeRef = useRef(onChange);
+	onChangeRef.current = onChange;
 
 	useEffect(() => {
 		if (isInitialMount.current) {
 			isInitialMount.current = false;
 			return;
 		}
-		onChange(tagsToEmailString(tags));
-	}, [tags, onChange]);
+		onChangeRef.current(tagsToEmailString(tags));
+	}, [tags]);
 
 	const handleSetTags = useCallback(
 		(newTags: TagType[] | ((prev: TagType[]) => TagType[])) => {
@@ -97,6 +102,103 @@ function EmailsTagField({
 	);
 }
 
+function parseDateTimeValue(value: string): { date: Date | undefined; time: string } {
+	if (!value) return { date: undefined, time: "09:00" };
+	try {
+		const d = new Date(value);
+		if (Number.isNaN(d.getTime())) return { date: undefined, time: "09:00" };
+		return {
+			date: d,
+			time: format(d, "HH:mm"),
+		};
+	} catch {
+		return { date: undefined, time: "09:00" };
+	}
+}
+
+function buildLocalDateTimeString(date: Date | undefined, time: string): string {
+	if (!date) return "";
+	const [hours, minutes] = time.split(":").map(Number);
+	const combined = new Date(date);
+	combined.setHours(hours ?? 9, minutes ?? 0, 0, 0);
+	const y = combined.getFullYear();
+	const m = String(combined.getMonth() + 1).padStart(2, "0");
+	const d = String(combined.getDate()).padStart(2, "0");
+	const h = String(combined.getHours()).padStart(2, "0");
+	const min = String(combined.getMinutes()).padStart(2, "0");
+	return `${y}-${m}-${d}T${h}:${min}:00`;
+}
+
+function DateTimePickerField({
+	id,
+	value,
+	onChange,
+}: {
+	id: string;
+	value: string;
+	onChange: (value: string) => void;
+}) {
+	const parsed = useMemo(() => parseDateTimeValue(value), [value]);
+	const [selectedDate, setSelectedDate] = useState<Date | undefined>(parsed.date);
+	const [time, setTime] = useState(parsed.time);
+	const [open, setOpen] = useState(false);
+
+	const handleDateSelect = useCallback(
+		(day: Date | undefined) => {
+			setSelectedDate(day);
+			onChange(buildLocalDateTimeString(day, time));
+			setOpen(false);
+		},
+		[time, onChange]
+	);
+
+	const handleTimeChange = useCallback(
+		(e: React.ChangeEvent<HTMLInputElement>) => {
+			const newTime = e.target.value;
+			setTime(newTime);
+			onChange(buildLocalDateTimeString(selectedDate, newTime));
+		},
+		[selectedDate, onChange]
+	);
+
+	const displayLabel = selectedDate
+		? `${format(selectedDate, "MMM d, yyyy")} at ${time}`
+		: "Pick date & time";
+
+	return (
+		<div className="flex gap-2">
+			<Popover open={open} onOpenChange={setOpen}>
+				<PopoverTrigger asChild>
+					<button
+						id={id}
+						type="button"
+						className="flex-1 flex items-center gap-2 h-9 rounded-md border border-input bg-transparent px-3 py-1 text-sm shadow-xs transition-[color,box-shadow] outline-none focus-visible:border-ring"
+					>
+						<CalendarIcon className="size-3.5 text-muted-foreground shrink-0" />
+						<span className={selectedDate ? "text-foreground" : "text-muted-foreground"}>
+							{displayLabel}
+						</span>
+					</button>
+				</PopoverTrigger>
+				<PopoverContent className="w-auto p-0" align="start">
+					<Calendar
+						mode="single"
+						selected={selectedDate}
+						onSelect={handleDateSelect}
+						defaultMonth={selectedDate}
+					/>
+				</PopoverContent>
+			</Popover>
+			<Input
+				type="time"
+				value={time}
+				onChange={handleTimeChange}
+				className="w-[120px] text-sm shrink-0 pl-1.5 [&::-webkit-calendar-picker-indicator]:order-first [&::-webkit-calendar-picker-indicator]:mr-1"
+			/>
+		</div>
+	);
+}
+
 export function HitlEditPanelContent({
 	title: initialTitle,
 	content: initialContent,
@@ -173,6 +275,12 @@ export function HitlEditPanelContent({
 									onChange={(v) => handleExtraFieldChange(field.key, v)}
 									placeholder={`Add ${field.label.toLowerCase()}`}
 								/>
+							) : field.type === "datetime-local" ? (
+								<DateTimePickerField
+									id={`extra-field-${field.key}`}
+									value={extraFieldValues[field.key] ?? ""}
+									onChange={(v) => handleExtraFieldChange(field.key, v)}
+								/>
 							) : field.type === "textarea" ? (
 								<Textarea
 									id={`extra-field-${field.key}`}
diff --git a/surfsense_web/components/tool-ui/google-calendar/create-event.tsx b/surfsense_web/components/tool-ui/google-calendar/create-event.tsx
index 61247ae4c..abd67e01a 100644
--- a/surfsense_web/components/tool-ui/google-calendar/create-event.tsx
+++ b/surfsense_web/components/tool-ui/google-calendar/create-event.tsx
@@ -2,7 +2,6 @@
 
 import { makeAssistantToolUI } from "@assistant-ui/react";
 import {
-	CalendarPlusIcon,
 	ClockIcon,
 	MapPinIcon,
 	UsersIcon,
@@ -250,7 +249,6 @@ function ApprovalCard({
 			{/* Header */}
 			<div className="flex items-start justify-between px-5 pt-5 pb-4 select-none">
 				<div className="flex items-center gap-2">
-					<CalendarPlusIcon className="size-4 text-muted-foreground shrink-0" />
 					<div>
 						<p className="text-sm font-semibold text-foreground">
 							{decided === "reject"
@@ -287,7 +285,7 @@ function ApprovalCard({
 								{ key: "start_datetime", label: "Start", type: "datetime-local", value: pendingEdits?.start_datetime ?? args.start_datetime ?? "" },
 								{ key: "end_datetime", label: "End", type: "datetime-local", value: pendingEdits?.end_datetime ?? args.end_datetime ?? "" },
 								{ key: "location", label: "Location", type: "text", value: pendingEdits?.location ?? args.location ?? "" },
-								{ key: "attendees", label: "Attendees (comma-separated emails)", type: "text", value: pendingEdits?.attendees ?? attendeesList.join(", ") },
+								{ key: "attendees", label: "Attendees", type: "emails", value: pendingEdits?.attendees ?? attendeesList.join(", ") },
 							];
 							openHitlEditPanel({
 								title: pendingEdits?.summary ?? (args.summary ?? ""),
diff --git a/surfsense_web/components/tool-ui/google-calendar/update-event.tsx b/surfsense_web/components/tool-ui/google-calendar/update-event.tsx
index 9c67f6c83..014293a18 100644
--- a/surfsense_web/components/tool-ui/google-calendar/update-event.tsx
+++ b/surfsense_web/components/tool-ui/google-calendar/update-event.tsx
@@ -328,7 +328,7 @@ function ApprovalCard({
 								{ key: "start_datetime", label: "Start", type: "datetime-local", value: proposedStart },
 								{ key: "end_datetime", label: "End", type: "datetime-local", value: proposedEnd },
 								{ key: "location", label: "Location", type: "text", value: proposedLocation },
-								{ key: "attendees", label: "Attendees (comma-separated emails)", type: "text", value: proposedAttendeesStr },
+								{ key: "attendees", label: "Attendees", type: "emails", value: proposedAttendeesStr },
 							];
 							openHitlEditPanel({
 								title: proposedSummary,