diff --git a/site/src/pages/AgentsPage/AgentSettingsPageView.tsx b/site/src/pages/AgentsPage/AgentSettingsPageView.tsx
index 3357751f58..41cb3b568a 100644
--- a/site/src/pages/AgentsPage/AgentSettingsPageView.tsx
+++ b/site/src/pages/AgentsPage/AgentSettingsPageView.tsx
@@ -274,6 +274,7 @@ const UsageContent: FC<UsageContentProps> = ({ now }) => {
 				<DateRangePicker
 					value={displayDateRange}
 					onChange={onDateRangeChange}
+					now={now?.toDate()}
 				/>
 			}
 		/>
diff --git a/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.stories.tsx b/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.stories.tsx
index 31c8786e26..e459aec31e 100644
--- a/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.stories.tsx
+++ b/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.stories.tsx
@@ -14,6 +14,9 @@ const defaultValue: DateRangeValue = {
 const meta: Meta<typeof DateRangePicker> = {
 	title: "components/DateRangePicker",
 	component: DateRangePicker,
+	args: {
+		now: fixedNow.toDate(),
+	},
 };
 
 export default meta;
@@ -61,7 +64,13 @@ export const Open: Story = {
 export const SelectPreset: Story = {
 	render: function SelectPresetStory() {
 		const [value, setValue] = useState<DateRangeValue>(defaultValue);
-		return <DateRangePicker value={value} onChange={setValue} />;
+		return (
+			<DateRangePicker
+				value={value}
+				onChange={setValue}
+				now={fixedNow.toDate()}
+			/>
+		);
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
@@ -93,7 +102,13 @@ export const SelectCalendarRange: Story = {
 			startDate: new Date("2025-03-01"),
 			endDate: new Date("2025-03-15"),
 		});
-		return <DateRangePicker value={value} onChange={setValue} />;
+		return (
+			<DateRangePicker
+				value={value}
+				onChange={setValue}
+				now={fixedNow.toDate()}
+			/>
+		);
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
@@ -119,7 +134,13 @@ export const SelectCalendarRange: Story = {
 export const CancelClosesWithoutApplying: Story = {
 	render: function CancelStory() {
 		const [value, setValue] = useState<DateRangeValue>(defaultValue);
-		return <DateRangePicker value={value} onChange={setValue} />;
+		return (
+			<DateRangePicker
+				value={value}
+				onChange={setValue}
+				now={fixedNow.toDate()}
+			/>
+		);
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
diff --git a/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.tsx b/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.tsx
index 0cd9e6d172..c6e1d649e7 100644
--- a/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.tsx
+++ b/site/src/pages/AgentsPage/components/DateRangePicker/DateRangePicker.tsx
@@ -27,44 +27,60 @@ interface DateRangePreset {
 	range: () => { from: Date; to: Date };
 }
 
-const defaultPresets: DateRangePreset[] = [
-	{
-		label: "Today",
-		range: () => ({ from: new Date(), to: new Date() }),
-	},
-	{
-		label: "Yesterday",
-		range: () => {
-			const d = dayjs().subtract(1, "day").toDate();
-			return { from: d, to: d };
+const buildDefaultPresets = (now?: Date): DateRangePreset[] => {
+	const getCurrentTime = () => dayjs(now ?? new Date());
+	return [
+		{
+			label: "Today",
+			range: () => {
+				const currentTime = getCurrentTime();
+				return { from: currentTime.toDate(), to: currentTime.toDate() };
+			},
 		},
-	},
-	{
-		label: "Last 7 days",
-		range: () => ({
-			from: dayjs().subtract(6, "day").toDate(),
-			to: new Date(),
-		}),
-	},
-	{
-		label: "Last 14 days",
-		range: () => ({
-			from: dayjs().subtract(13, "day").toDate(),
-			to: new Date(),
-		}),
-	},
-	{
-		label: "Last 30 days",
-		range: () => ({
-			from: dayjs().subtract(29, "day").toDate(),
-			to: new Date(),
-		}),
-	},
-];
+		{
+			label: "Yesterday",
+			range: () => {
+				const d = getCurrentTime().subtract(1, "day").toDate();
+				return { from: d, to: d };
+			},
+		},
+		{
+			label: "Last 7 days",
+			range: () => {
+				const currentTime = getCurrentTime();
+				return {
+					from: currentTime.subtract(6, "day").toDate(),
+					to: currentTime.toDate(),
+				};
+			},
+		},
+		{
+			label: "Last 14 days",
+			range: () => {
+				const currentTime = getCurrentTime();
+				return {
+					from: currentTime.subtract(13, "day").toDate(),
+					to: currentTime.toDate(),
+				};
+			},
+		},
+		{
+			label: "Last 30 days",
+			range: () => {
+				const currentTime = getCurrentTime();
+				return {
+					from: currentTime.subtract(29, "day").toDate(),
+					to: currentTime.toDate(),
+				};
+			},
+		},
+	];
+};
 
 interface DateRangePickerProps {
 	value: DateRangeValue;
 	onChange: (value: DateRangeValue) => void;
+	now?: Date;
 	presets?: DateRangePreset[];
 }
 
@@ -74,10 +90,11 @@ interface DateRangePickerProps {
  * rounded up to the next hour (if it falls on today) or to the start of
  * the following day.
  */
-function toBoundary(from: Date, to: Date): DateRangeValue {
+function toBoundary(from: Date, to: Date, now: Date): DateRangeValue {
+	const currentTime = dayjs(now);
 	const start = dayjs(from).startOf("day").toDate();
-	const end = dayjs(to).isSame(dayjs(), "day")
-		? dayjs().startOf("hour").add(1, "hour").toDate()
+	const end = dayjs(to).isSame(currentTime, "day")
+		? currentTime.startOf("hour").add(1, "hour").toDate()
 		: dayjs(to).startOf("day").add(1, "day").toDate();
 	return { startDate: start, endDate: end };
 }
@@ -100,9 +117,12 @@ function fromBoundary(value: DateRangeValue): DayPickerDateRange {
 export const DateRangePicker: FC<DateRangePickerProps> = ({
 	value,
 	onChange,
-	presets = defaultPresets,
+	now,
+	presets,
 }) => {
 	const [open, setOpen] = useState(false);
+	const currentTime = now ?? new Date();
+	const resolvedPresets = presets ?? buildDefaultPresets(now);
 
 	// Internal selection state kept separate from the committed value
 	// so the user can freely adjust the range before applying. This
@@ -113,7 +133,7 @@ export const DateRangePicker: FC<DateRangePickerProps> = ({
 
 	const commit = () => {
 		if (selection?.from && selection?.to) {
-			onChange(toBoundary(selection.from, selection.to));
+			onChange(toBoundary(selection.from, selection.to, now ?? new Date()));
 		}
 		setOpen(false);
 	};
@@ -122,7 +142,7 @@ export const DateRangePicker: FC<DateRangePickerProps> = ({
 		const { from, to } = preset.range();
 		setSelection({ from, to });
 		// Presets are a complete selection — commit immediately.
-		onChange(toBoundary(from, to));
+		onChange(toBoundary(from, to, now ?? new Date()));
 		setOpen(false);
 	};
 
@@ -168,7 +188,7 @@ export const DateRangePicker: FC<DateRangePickerProps> = ({
 				<div className="flex">
 					{/* Presets sidebar */}
 					<div className="flex flex-col border-r border-border-default p-2 text-sm">
-						{presets.map((preset) => (
+						{resolvedPresets.map((preset) => (
 							<button
 								key={preset.label}
 								type="button"
@@ -223,7 +243,7 @@ export const DateRangePicker: FC<DateRangePickerProps> = ({
 								selected={selection}
 								onSelect={handleCalendarSelect}
 								numberOfMonths={2}
-								disabled={{ after: new Date() }}
+								disabled={{ after: currentTime }}
 							/>
 						</div>
 
diff --git a/site/src/pages/CreateTokenPage/CreateTokenForm.tsx b/site/src/pages/CreateTokenPage/CreateTokenForm.tsx
index d11a38540b..cd2a5f14b4 100644
--- a/site/src/pages/CreateTokenPage/CreateTokenForm.tsx
+++ b/site/src/pages/CreateTokenPage/CreateTokenForm.tsx
@@ -33,6 +33,7 @@ interface CreateTokenFormProps {
 	setFormError: (arg0: unknown) => void;
 	isCreating: boolean;
 	creationFailed: boolean;
+	now?: Date;
 }
 
 export const CreateTokenForm: FC<CreateTokenFormProps> = ({
@@ -42,6 +43,7 @@ export const CreateTokenForm: FC<CreateTokenFormProps> = ({
 	setFormError,
 	isCreating,
 	creationFailed,
+	now,
 }) => {
 	const navigate = useNavigate();
 
@@ -49,6 +51,7 @@ export const CreateTokenForm: FC<CreateTokenFormProps> = ({
 	const [lifetimeDays, setLifetimeDays] = useState<number | string>(
 		determineDefaultLtValue(maxTokenLifetime),
 	);
+	const currentTime = dayjs(now ?? new Date());
 
 	// biome-ignore lint/correctness/useExhaustiveDependencies: adding form will cause an infinite loop
 	useEffect(() => {
@@ -86,7 +89,7 @@ export const CreateTokenForm: FC<CreateTokenFormProps> = ({
 						<>
 							The token will expire on{" "}
 							<span data-chromatic="ignore">
-								{dayjs()
+								{currentTime
 									.add(form.values.lifetime, "days")
 									.utc()
 									.format("MMMM DD, YYYY")}
diff --git a/site/src/pages/CreateTokenPage/CreateTokenPage.stories.tsx b/site/src/pages/CreateTokenPage/CreateTokenPage.stories.tsx
index 8885dc5841..d23b69df0e 100644
--- a/site/src/pages/CreateTokenPage/CreateTokenPage.stories.tsx
+++ b/site/src/pages/CreateTokenPage/CreateTokenPage.stories.tsx
@@ -17,4 +17,8 @@ const meta: Meta<typeof CreateTokenPage> = {
 export default meta;
 type Story = StoryObj<typeof CreateTokenPage>;
 
-export const Default: Story = {};
+export const Default: Story = {
+	args: {
+		now: new Date("2026-03-12T12:00:00Z"),
+	},
+};
diff --git a/site/src/pages/CreateTokenPage/CreateTokenPage.tsx b/site/src/pages/CreateTokenPage/CreateTokenPage.tsx
index 4c39af9741..f058e170df 100644
--- a/site/src/pages/CreateTokenPage/CreateTokenPage.tsx
+++ b/site/src/pages/CreateTokenPage/CreateTokenPage.tsx
@@ -19,7 +19,11 @@ const initialValues: CreateTokenData = {
 	lifetime: 30,
 };
 
-const CreateTokenPage: FC = () => {
+type CreateTokenPageProps = {
+	now?: Date;
+};
+
+const CreateTokenPage: FC<CreateTokenPageProps> = ({ now }) => {
 	const navigate = useNavigate();
 
 	const {
@@ -105,6 +109,7 @@ const CreateTokenPage: FC = () => {
 					setFormError={setFormError}
 					isCreating={isCreating}
 					creationFailed={creationFailed}
+					now={now}
 				/>
 
 				<ConfirmDialog
diff --git a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.stories.tsx b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.stories.tsx
index 859c49e434..f9ee370b37 100644
--- a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.stories.tsx
+++ b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard.stories.tsx
@@ -6,9 +6,8 @@ import { expect, fn, within } from "storybook/test";
 
 import { LicenseCard } from "./LicenseCard";
 
-const FIXED_NOW = dayjs().startOf("day");
-const YESTERDAY = FIXED_NOW.subtract(1, "day").unix();
-const NEXT_WEEK = FIXED_NOW.add(7, "day").unix();
+const EXPIRED_DATE = dayjs("2000-01-01T12:00:00Z").unix();
+const FUTURE_START_DATE = dayjs("2099-01-01T12:00:00Z").unix();
 
 const meta: Meta<typeof LicenseCard> = {
 	title: "pages/DeploymentSettingsPage/LicensesSettingsPage/LicenseCard",
@@ -176,7 +175,7 @@ export const ExpiredAIGovernanceOverageShowsExpired: Story = {
 			...MockLicenseResponse[1],
 			claims: {
 				...MockLicenseResponse[1].claims,
-				license_expires: YESTERDAY,
+				license_expires: EXPIRED_DATE,
 				features: {
 					...MockLicenseResponse[1].claims.features,
 					ai_governance_user_limit: 1000,
@@ -208,7 +207,7 @@ export const ExpiredAIGovernanceInGracePeriodShowsExceeded: Story = {
 			...MockLicenseResponse[1],
 			claims: {
 				...MockLicenseResponse[1].claims,
-				license_expires: YESTERDAY,
+				license_expires: EXPIRED_DATE,
 				features: {
 					...MockLicenseResponse[1].claims.features,
 					ai_governance_user_limit: 1000,
@@ -238,7 +237,7 @@ export const NotYetValid: Story = {
 			...MockLicenseResponse[1],
 			claims: {
 				...MockLicenseResponse[1].claims,
-				nbf: NEXT_WEEK,
+				nbf: FUTURE_START_DATE,
 			},
 		},
 	},
@@ -254,7 +253,7 @@ export const FutureAIGovernanceOverageShowsStartsOn: Story = {
 			...MockLicenseResponse[1],
 			claims: {
 				...MockLicenseResponse[1].claims,
-				nbf: NEXT_WEEK,
+				nbf: FUTURE_START_DATE,
 				features: {
 					...MockLicenseResponse[1].claims.features,
 					ai_governance_user_limit: 1000,
@@ -286,7 +285,7 @@ export const FutureAIGovernanceUsageShowsNoCurrentSeats: Story = {
 			...MockLicenseResponse[1],
 			claims: {
 				...MockLicenseResponse[1].claims,
-				nbf: NEXT_WEEK,
+				nbf: FUTURE_START_DATE,
 				features: {
 					...MockLicenseResponse[1].claims.features,
 					ai_governance_user_limit: 1000,
diff --git a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicensesSettingsPage.stories.tsx b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicensesSettingsPage.stories.tsx
index 95e4abeb6d..1b734582a0 100644
--- a/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicensesSettingsPage.stories.tsx
+++ b/site/src/pages/DeploymentSettingsPage/LicensesSettingsPage/LicensesSettingsPage.stories.tsx
@@ -23,6 +23,8 @@ const USER_STATUS_COUNTS_QUERY = {
 	data: { active: [] },
 };
 
+const STORY_NOW = dayjs("2099-01-01T12:00:00Z");
+
 const withBaseQueries = ({
 	entitlements = MockEntitlements,
 	licenses = MockLicenseResponse,
@@ -89,8 +91,8 @@ const createLicense = ({
 	addons?: string[];
 }) => ({
 	id,
-	uploaded_at: String(dayjs().subtract(uploadedDaysAgo, "day").unix()),
-	expires_at: String(dayjs().add(expiresInDays, "day").unix()),
+	uploaded_at: String(STORY_NOW.subtract(uploadedDaysAgo, "day").unix()),
+	expires_at: String(STORY_NOW.add(expiresInDays, "day").unix()),
 	uuid,
 	claims: {
 		trial: false,
@@ -102,8 +104,8 @@ const createLicense = ({
 			user_limit: userLimit,
 		},
 		addons,
-		license_expires: dayjs().add(licenseExpiresInDays, "day").unix(),
-		nbf: dayjs().add(nbfOffsetDays, "day").unix(),
+		license_expires: STORY_NOW.add(licenseExpiresInDays, "day").unix(),
+		nbf: STORY_NOW.add(nbfOffsetDays, "day").unix(),
 	},
 });
 
diff --git a/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsControls.stories.tsx b/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsControls.stories.tsx
index 1e1e0e8198..a5e12fa0dd 100644
--- a/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsControls.stories.tsx
+++ b/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsControls.stories.tsx
@@ -17,6 +17,7 @@ const defaultArgs: Partial<ComponentProps<typeof TemplateInsightsControls>> = {
 		startDate: new Date("2025-08-05"),
 		endDate: new Date("2025-08-07"),
 	},
+	now: new Date("2025-08-07T12:00:00Z"),
 	setDateRange: () => {},
 	searchParams: new URLSearchParams(),
 	setSearchParams: () => {},
diff --git a/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsPage.tsx b/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsPage.tsx
index fc7747690e..444b5a10f1 100644
--- a/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsPage.tsx
+++ b/site/src/pages/TemplatePage/TemplateInsightsPage/TemplateInsightsPage.tsx
@@ -142,6 +142,7 @@ interface TemplateInsightsControlsProps {
 	setDateRange: (value: DateRangeValue) => void;
 	searchParams: URLSearchParams;
 	setSearchParams: SetURLSearchParams;
+	now?: Date;
 }
 
 export const TemplateInsightsControls: FC<TemplateInsightsControlsProps> = ({
@@ -150,6 +151,7 @@ export const TemplateInsightsControls: FC<TemplateInsightsControlsProps> = ({
 	setDateRange,
 	searchParams,
 	setSearchParams,
+	now,
 }) => {
 	return (
 		<>
@@ -165,7 +167,7 @@ export const TemplateInsightsControls: FC<TemplateInsightsControlsProps> = ({
 				}}
 			/>
 			{interval === "day" ? (
-				<DailyPicker value={dateRange} onChange={setDateRange} />
+				<DailyPicker value={dateRange} onChange={setDateRange} now={now} />
 			) : (
 				<WeekPicker value={dateRange} onChange={setDateRange} />
 			)}