diff --git a/apps/www/src/client/App.tsx b/apps/www/src/client/App.tsx
index 33a8e30..9df26bd 100644
--- a/apps/www/src/client/App.tsx
+++ b/apps/www/src/client/App.tsx
@@ -3306,7 +3306,19 @@ function Dashboard({
 			: []),
 		// Narrower than the two above: the drop mints tokens, and www's route is developer-only.
 		...(isDeveloper()
-			? [{ id: 'tokens', label: 'Token drop', render: () => <TokenDropForm /> }]
+			? [
+					{
+						id: 'tokens',
+						label: 'Token drop',
+						// Two audiences for one gift: whoever is online now, or whoever holds a Discord role.
+						render: () => (
+							<>
+								<TokenDropForm />
+								<RoleTokenDropForm />
+							</>
+						),
+					},
+				]
 			: []),
 	]
 	const [active, setActive] = useState(sections[0].id)
@@ -3682,6 +3694,97 @@ function TokenDropForm() {
 	)
 }
 
+/**
+ * Developer-only: give every player whose Discord link holds a role the same number of
+ * tokens, in a gift box carrying the operator's message — the token drop's sibling, with a
+ * different audience. Offline is the point: the box waits for whoever isn't signed in.
+ *
+ * The audience is the roles the website recorded at each player's benefits claim and
+ * refreshes once a day, so it trails Discord by up to a day and never includes a member who
+ * hasn't claimed; the copy says so. Same cap as the online drop, repeated on the input.
+ */
+function RoleTokenDropForm() {
+	const [roleId, setRoleId] = useState('')
+	const [message, setMessage] = useState('')
+	const [tokens, setTokens] = useState('')
+	const { pending, error, done, run } = useAction()
+
+	return (
+		<section className="card">
+			<h2>Discord role drop</h2>
+			<p className="muted">
+				Give everyone holding a Discord role the same number of tokens, whether or not they are
+				online — a player who is signed out finds the gift box waiting. Only players who have
+				claimed benefits on this site are counted, and their roles are refreshed once a day, so a
+				role given or taken since then isn&apos;t seen yet. Up to {MAX_TOKEN_DROP.toLocaleString()}{' '}
+				tokens each.
+			</p>
+			<form
+				onSubmit={(e) => {
+					e.preventDefault()
+					void run(async () => {
+						const amount = Number(tokens)
+						const role = roleId.trim()
+						const res = await call<{ paid: number[] }>(
+							`/api/staff/discord-roles/${encodeURIComponent(role)}/gift-tokens`,
+							{ authed: true, json: { amount, message: message.trim() } }
+						)
+						setTokens('')
+						setMessage('')
+						const n = res.paid.length
+						return `Sent ${amount.toLocaleString()} tokens to ${n} player${n === 1 ? '' : 's'} holding role ${role}.`
+					})
+				}}
+			>
+				<label>
+					Discord role id
+					<input
+						type="text"
+						inputMode="numeric"
+						pattern="[0-9]+"
+						value={roleId}
+						placeholder="1077000000000000001"
+						required
+						onChange={(e) => setRoleId(e.target.value)}
+					/>
+					<span className="hint">
+						The role&apos;s numeric id, from Discord&apos;s role settings (Copy Role ID), not its
+						name.
+					</span>
+				</label>
+				<label>
+					Gift box message
+					<textarea
+						value={message}
+						rows={3}
+						maxLength={256}
+						placeholder="Thanks for supporting the server!"
+						onChange={(e) => setMessage(e.target.value)}
+						required
+					/>
+				</label>
+				<label>
+					Tokens per player
+					<input
+						type="number"
+						min={1}
+						max={MAX_TOKEN_DROP}
+						step={1}
+						value={tokens}
+						required
+						onChange={(e) => setTokens(e.target.value)}
+					/>
+				</label>
+				{error && <p className="error">{error}</p>}
+				{done && <p className="ok">{done}</p>}
+				<button type="submit" disabled={pending}>
+					{pending ? 'Sending…' : 'Send to everyone with the role'}
+				</button>
+			</form>
+		</section>
+	)
+}
+
 /**
  * Change the account's username — the name used to sign in, here and in the game.
  *
diff --git a/apps/www/src/staff.ts b/apps/www/src/staff.ts
index e9850c0..c34cbe6 100644
--- a/apps/www/src/staff.ts
+++ b/apps/www/src/staff.ts
@@ -10,6 +10,7 @@ import {
 	movePlayerToDorm,
 	writeAuditLog,
 } from '@repo/domain'
+import { PlatformType } from '@repo/domain/src/enums'
 import { intVar, logger } from '@repo/hono-helpers'
 import { validateAndGetAccountId, validateAndGetRoles } from '@repo/jwt'
 
@@ -31,6 +32,9 @@ import {
 	searchReports,
 } from '../../api/src/reports-db'
 import { getWarningsAgainst } from '../../api/src/warnings-db'
+// The platform links, owned by `auth`: a Discord link carries the roles its member held at
+// their claim or the last daily sweep (discord-roles.ts), which is what the role drop reads.
+import { getLinksForPlatform } from '../../auth/src/platform-db'
 // Balances, owned by `econ`. A staff token gift is the same credit econ's own faucets make.
 import {
 	ALL_PLATFORMS,
@@ -955,6 +959,79 @@ export async function giftOnlineTokensHandler(c: Context<App>) {
 	return c.json({ amount, message, paid })
 }
 
+/**
+ * Send tokens to EVERYONE HOLDING A DISCORD ROLE — online or not. The account page's second
+ * drop, beside the one to everyone online: the same box, the same cap, a different audience.
+ *
+ * The audience is every account whose Discord link records the role: the snapshot the
+ * benefits claim wrote and the daily sweep (discord-roles.ts) refreshes, read when the button
+ * is pressed. Nothing asks Discord here — a member who gained the role since the last sweep
+ * is missed until the next one, and one who lost it is still paid until then; the form says
+ * as much. A player who holds the role in the guild but never claimed on the website has no
+ * link, and so is not in the audience however many roles they hold there. The link is the
+ * unit, so a Discord identity linked to two accounts pays both; an account is paid once
+ * whatever its links say.
+ *
+ * Offline is the point: the econ cron's supporter gift (discord-role-gift.ts) is this on a
+ * schedule, and this is the hand-run version with an operator's amount and message on it. A
+ * player who isn't signed in meets the box in `GET /api/avatar/v2/gifts` and the balance on
+ * their next read, as they do for every box the server hands over.
+ *
+ * The role is a Discord snowflake — all digits, compared exactly, as the sweep stores them.
+ * The amount is bounded as the online drop's is ({@link MAX_TOKEN_DROP} each, positive only):
+ * this one multiplies by a role's whole membership, which can be larger than the server has
+ * ever had online at once. The message is required for the same reason.
+ */
+export async function giftRoleTokensHandler(c: Context<App>) {
+	const roleId = c.req.param('roleId') ?? ''
+	if (!/^\d+$/.test(roleId)) {
+		return c.json({ error: 'A Discord role id is all digits' }, 400)
+	}
+
+	const body = (await c.req.json().catch(() => ({}))) as { amount?: unknown; message?: unknown }
+	const amount = Number(body.amount)
+	if (!Number.isInteger(amount) || amount <= 0) {
+		return c.json({ error: 'Enter a whole number of tokens greater than 0' }, 400)
+	}
+	if (amount > MAX_TOKEN_DROP) {
+		return c.json(
+			{ error: `A token drop can carry at most ${MAX_TOKEN_DROP.toLocaleString()} tokens each` },
+			400
+		)
+	}
+	if (typeof body.message !== 'string' || body.message.trim() === '') {
+		return c.json({ error: 'Enter the message for the gift box' }, 400)
+	}
+	const message = giftMessage(body)
+	if (message === undefined) return c.json({ error: GIFT_MESSAGE_TOO_LONG }, 400)
+
+	const links = await getLinksForPlatform(c.env.DB, PlatformType.Discord)
+	const playerIds = [
+		...new Set(links.filter((l) => l.roles.includes(roleId)).map((l) => l.accountId)),
+	]
+	if (playerIds.length === 0) {
+		return c.json({ error: 'No linked account holds that Discord role' }, 404)
+	}
+
+	const startingTokens = intVar(c.env.STARTING_TOKENS, DEFAULT_STARTING_TOKENS)
+	const paid: number[] = []
+	for (const playerId of playerIds) {
+		// A positive amount never comes back null: nothing to skip.
+		if ((await sendTokens(c, playerId, amount, startingTokens, message)) !== null) {
+			paid.push(playerId)
+		}
+	}
+
+	await recordPlayerAudit(c, 'gift_tokens_role', { roleId, amount, message, paid })
+	logger.info('staff dropped tokens on a discord role', {
+		moderatorId: staffId(c),
+		roleId,
+		amount,
+		paidCount: paid.length,
+	})
+	return c.json({ roleId, amount, message, paid })
+}
+
 /**
  * Give a player XP, in a gift box — the way a game reward pays its XP. The XP is banked
  * here (the box, like every box, grants nothing when opened) and spent on any levels it now
diff --git a/apps/www/src/test/integration/api.test.ts b/apps/www/src/test/integration/api.test.ts
index c3fb185..85ec937 100644
--- a/apps/www/src/test/integration/api.test.ts
+++ b/apps/www/src/test/integration/api.test.ts
@@ -860,7 +860,11 @@ it('refuses every staff endpoint without a token, and without a staff role', asy
 		'/api/staff/players/1/username-changes',
 		'/api/staff/players/1/clear-password',
 	]
-	writes.push('/api/staff/rooms/1/gift-tokens', '/api/staff/online/gift-tokens')
+	writes.push(
+		'/api/staff/rooms/1/gift-tokens',
+		'/api/staff/online/gift-tokens',
+		'/api/staff/discord-roles/1/gift-tokens'
+	)
 	for (const path of writes) {
 		expect((await SELF.fetch(`https://example.com${path}`, { method: 'POST' })).status).toBe(401)
 		const res = await SELF.fetch(`https://example.com${path}`, {
@@ -1808,6 +1812,101 @@ it('refuses a token drop over the cap, without a message, or with nobody online'
 	expect((await drop({ amount: 1_000, message: 'hi' })).status).toBe(404)
 })
 
+// The role drop's audience is the Discord links that record the role — offline included,
+// since that is the point — and nobody else: a link holding other roles, a link holding none,
+// a player with no link at all. The same Discord identity on two accounts pays both.
+it('drops tokens on every account whose Discord link holds the role, online or not', async () => {
+	const ROLE = '1077000000000000777'
+	const OTHER = '1077000000000000778'
+	await linkPlatformIdentity(env.DB, 8390, PlatformType.Discord, '900000000000008390', [ROLE])
+	await linkPlatformIdentity(env.DB, 8391, PlatformType.Discord, '900000000000008391', [
+		OTHER,
+		ROLE,
+	])
+	await linkPlatformIdentity(env.DB, 8392, PlatformType.Discord, '900000000000008392', [OTHER])
+	await linkPlatformIdentity(env.DB, 8393, PlatformType.Discord, '900000000000008393', [])
+	// One Discord user, two accounts: both links hold the role.
+	await linkPlatformIdentity(env.DB, 8394, PlatformType.Discord, '900000000000008394', [ROLE])
+	await linkPlatformIdentity(env.DB, 8395, PlatformType.Discord, '900000000000008394', [ROLE])
+	// Only one of them is online; the rest are paid anyway.
+	await env.DB.prepare('DELETE FROM presence').run()
+	await setPresence(env.DB, {
+		accountId: 8390,
+		roomInstance: null,
+		statusVisibility: 0,
+		deviceClass: 0,
+		vrMovementMode: 0,
+		platform: 4,
+		appVersion: 'test',
+	})
+
+	const res = await devPost(`/api/staff/discord-roles/${ROLE}/gift-tokens`, 8110, {
+		amount: 250,
+		message: 'Thanks for supporting the server!',
+	})
+	expect(res.status).toBe(200)
+	const body = (await res.json()) as {
+		roleId: string
+		amount: number
+		message: string
+		paid: number[]
+	}
+	expect(body.roleId).toBe(ROLE)
+	expect(body.amount).toBe(250)
+	expect(body.message).toBe('Thanks for supporting the server!')
+	expect([...body.paid].sort((a, b) => a - b)).toEqual([8390, 8391, 8394, 8395])
+
+	for (const playerId of [8390, 8391, 8394, 8395]) {
+		await expect(
+			getBalance(env.DB, playerId, CurrencyType.RecCenterTokens, DEFAULT_STARTING_TOKENS)
+		).resolves.toBe(DEFAULT_STARTING_TOKENS + 250)
+		const gifts = await getPendingGifts(env.DB, playerId)
+		expect(gifts).toHaveLength(1)
+		expect(gifts[0]).toMatchObject({
+			Currency: 250,
+			CurrencyType: CurrencyType.RecCenterTokens,
+			AvatarItemType: null,
+			Message: 'Thanks for supporting the server!',
+		})
+	}
+	for (const playerId of [8392, 8393]) {
+		expect(await getPendingGifts(env.DB, playerId)).toEqual([])
+		await expect(
+			getBalance(env.DB, playerId, CurrencyType.RecCenterTokens, DEFAULT_STARTING_TOKENS)
+		).resolves.toBe(DEFAULT_STARTING_TOKENS)
+	}
+
+	const { results } = await env.DB.prepare(
+		`SELECT player_id, data FROM audit_log WHERE action = 'gift_tokens_role'`
+	).all<{ player_id: number; data: string }>()
+	expect(results).toHaveLength(1)
+	expect(results[0].player_id).toBe(8110)
+	expect(JSON.parse(results[0].data)).toMatchObject({
+		roleId: ROLE,
+		amount: 250,
+		message: 'Thanks for supporting the server!',
+	})
+})
+
+// Same bounds as the online drop, plus the role has to be a snowflake, and a role nobody's
+// link records is a 404 rather than a silent success.
+it('refuses a role drop over the cap, without a message, with a bad role, or with no holders', async () => {
+	const drop = (role: string, body: unknown) =>
+		devPost(`/api/staff/discord-roles/${role}/gift-tokens`, 8110, body)
+	await linkPlatformIdentity(env.DB, 8396, PlatformType.Discord, '900000000000008396', [
+		'1077000000000000779',
+	])
+	expect((await drop('1077000000000000779', { amount: 1_001, message: 'hi' })).status).toBe(400)
+	expect((await drop('1077000000000000779', { amount: 0, message: 'hi' })).status).toBe(400)
+	expect((await drop('1077000000000000779', { amount: -5, message: 'hi' })).status).toBe(400)
+	expect((await drop('1077000000000000779', { amount: 10, message: '   ' })).status).toBe(400)
+	expect((await drop('1077000000000000779', { amount: 10 })).status).toBe(400)
+	expect((await drop('supporters', { amount: 10, message: 'hi' })).status).toBe(400)
+	expect((await drop('1077000000000000780', { amount: 10, message: 'hi' })).status).toBe(404)
+	// Nothing above paid anyone.
+	expect(await getPendingGifts(env.DB, 8396)).toEqual([])
+})
+
 // Zero is a real gift here: nothing moves, and the player gets an empty box.
 it('sends an empty box on a zero token gift', async () => {
 	await updateAccount(env.DB, 8361, { username: 'Emptyhanded' })
diff --git a/apps/www/src/www.app.ts b/apps/www/src/www.app.ts
index b7f07c6..ceb59b9 100644
--- a/apps/www/src/www.app.ts
+++ b/apps/www/src/www.app.ts
@@ -48,6 +48,7 @@ import {
 	getReportHandler,
 	giftItemHandler,
 	giftOnlineTokensHandler,
+	giftRoleTokensHandler,
 	giftRoomTokensHandler,
 	giftTokensHandler,
 	giftXpHandler,
@@ -556,6 +557,9 @@ const app = new Hono<App>()
 	.post('/api/staff/rooms/:roomId/gift-tokens', requireDeveloper, giftRoomTokensHandler)
 	// The account page's token drop: the same gift to everyone online at once.
 	.post('/api/staff/online/gift-tokens', requireDeveloper, giftOnlineTokensHandler)
+	// Its sibling: the same gift to every account whose Discord link holds a role, offline
+	// included — the supporter cron's audience, with an operator's amount and message.
+	.post('/api/staff/discord-roles/:roleId/gift-tokens', requireDeveloper, giftRoleTokensHandler)
 	.post('/api/staff/players/:id/username-changes', addUsernameChangeHandler)
 	.post('/api/staff/players/:id/clear-password', clearPasswordHandler)