diff --git a/server/api/service/cron/waitlist-drip.get.ts b/server/api/service/cron/waitlist-drip.get.ts
new file mode 100644
index 0000000..37e8eb4
--- /dev/null
+++ b/server/api/service/cron/waitlist-drip.get.ts
@@ -0,0 +1,123 @@
+import { defineEventHandler } from 'h3'
+import { InvitationCode } from '../../../models/InvitationCode'
+import { WaitlistEntry } from '../../../models/WaitlistEntry'
+import { sendMail } from '../../../utils/notifications'
+import { generateInvitationCode, renderInvitationEmail, renderInvitationText } from '../../../utils/invitations'
+
+const DAY_MS = 1000 * 60 * 60 * 24
+const INVITATION_DELAY_DAYS = 5
+const FEEDBACK_DELAY_DAYS = 14
+
+export default defineEventHandler(async () => {
+  const now = new Date()
+  const invitationCutoff = new Date(now.getTime() - INVITATION_DELAY_DAYS * DAY_MS)
+  const feedbackCutoff = new Date(now.getTime() - FEEDBACK_DELAY_DAYS * DAY_MS)
+
+  const invitationCandidates = await WaitlistEntry.find({
+    joinedAt: { $lte: invitationCutoff },
+    $and: [
+      { $or: [{ invitationSentAt: { $exists: false } }, { invitationSentAt: null }] },
+      { $or: [{ activatedAt: { $exists: false } }, { activatedAt: null }] },
+    ],
+  }).exec()
+
+  let invitationsSent = 0
+
+  for (const entry of invitationCandidates) {
+    const email = entry.email?.trim()
+    if (!email) {
+      continue
+    }
+
+    let invitation = entry.invitationCode ? await InvitationCode.findById(entry.invitationCode) : null
+
+    if (invitation?.usedAt) {
+      continue
+    }
+
+    const sentAt = new Date()
+
+    if (!invitation) {
+      const code = generateInvitationCode()
+      invitation = await InvitationCode.create({
+        code,
+        createdAt: sentAt,
+        channel: 'admin',
+        label: `Waitlist: ${email}`,
+      })
+      entry.invitationCode = invitation._id
+    }
+
+    entry.invitationSentAt = sentAt
+    await entry.save()
+
+    const html = await renderInvitationEmail(invitation.code)
+    const text = renderInvitationText(invitation.code)
+
+    await sendMail({
+      to: email,
+      subject: 'Your OpenSquawk invite code',
+      text,
+      html,
+    })
+
+    invitationsSent += 1
+  }
+
+  const feedbackCandidates = await WaitlistEntry.find({
+    invitationSentAt: { $lte: feedbackCutoff },
+    $or: [
+      { feedbackRequestedAt: { $exists: false } },
+      { feedbackRequestedAt: null },
+    ],
+  }).exec()
+
+  let feedbackRequests = 0
+
+  for (const entry of feedbackCandidates) {
+    const email = entry.email?.trim()
+    if (!email) {
+      continue
+    }
+
+    const requestedAt = new Date()
+
+    const text = [
+      'Hi there,',
+      '',
+      "It's been a little while since we sent your invite, and we would love to hear your thoughts.",
+      '',
+      'Share your feedback here:',
+      'https://opensquawk.de/feedback',
+      '',
+      'Thank you for helping us improve OpenSquawk!',
+    ].join('\n')
+
+    const html = [
+      '<p>Hi there,</p>',
+      '<p>It\'s been a little while since we sent your invite, and we would love to hear your thoughts.</p>',
+      '<p><a href="https://opensquawk.de/feedback">Share your feedback here</a></p>',
+      '<p>Thank you for helping us improve OpenSquawk!</p>',
+    ].join('')
+
+    await sendMail({
+      to: email,
+      subject: 'How is your OpenSquawk experience?',
+      text,
+      html,
+    })
+
+    entry.feedbackRequestedAt = requestedAt
+    await entry.save()
+
+    feedbackRequests += 1
+  }
+
+  console.log(`[waitlist-drip] invitations sent: ${invitationsSent}`)
+  console.log(`[waitlist-drip] feedback requests sent: ${feedbackRequests}`)
+
+  return {
+    invitationsSent,
+    feedbackRequests,
+  }
+})
diff --git a/server/models/WaitlistEntry.ts b/server/models/WaitlistEntry.ts
index 5e1ff55..2758fc4 100644
--- a/server/models/WaitlistEntry.ts
+++ b/server/models/WaitlistEntry.ts
@@ -15,6 +15,7 @@ export interface WaitlistEntryDocument extends mongoose.Document {
   updatesOptedInAt?: Date
   invitationCode?: mongoose.Types.ObjectId
   invitationSentAt?: Date
+  feedbackRequestedAt?: Date
 }
 
 const waitlistSchema = new mongoose.Schema<WaitlistEntryDocument>({
@@ -30,6 +31,7 @@ const waitlistSchema = new mongoose.Schema<WaitlistEntryDocument>({
   updatesOptedInAt: { type: Date },
   invitationCode: { type: Schema.Types.ObjectId, ref: 'InvitationCode' },
   invitationSentAt: { type: Date },
+  feedbackRequestedAt: { type: Date },
 })
 
 export const WaitlistEntry =