diff --git a/convex/cleanup.ts b/convex/cleanup.ts
index 5fcfcd655..3ef9b914f 100644
--- a/convex/cleanup.ts
+++ b/convex/cleanup.ts
@@ -1,7 +1,7 @@
 import { v } from "convex/values";
 import { internalMutation, internalQuery, type MutationCtx } from "./_generated/server";
 import { internal } from "./_generated/api";
-import type { Id } from "./_generated/dataModel";
+import type { Doc, Id } from "./_generated/dataModel";
 
 const delayInMs = parseFloat(process.env.DEBUG_FILE_CLEANUP_DELAY_MS ?? "500");
 const debugFileCleanupBatchSize = parseInt(process.env.DEBUG_FILE_CLEANUP_BATCH_SIZE ?? "100");
@@ -363,3 +363,142 @@ export const getReferencedFiles = internalQuery({
     }
   },
 });
+
+const maxMembersToProcess = 1000;
+export const deleteDataForDeletedMembers = internalMutation({
+  args: {},
+  handler: async (ctx) => {
+    const deletedMembers = await ctx.db
+      .query("convexMembers")
+      .withIndex("byIsDeletedAccount", (q) => q.eq("isDeletedAccount", true))
+      .take(maxMembersToProcess);
+
+    console.log(`Processing ${deletedMembers.length} soft-deleted members`);
+
+    for (const deletedMember of deletedMembers) {
+      await ctx.scheduler.runAfter(calculateJitteredDelay(50, 0.2), internal.cleanup.deleteDataForMember, {
+        memberId: deletedMember._id,
+      });
+    }
+  },
+});
+
+export const deleteDataForMember = internalMutation({
+  args: { memberId: v.id("convexMembers") },
+  handler: async (ctx, { memberId }) => {
+    const member: Doc<"convexMembers"> = (await ctx.db.get(memberId)) as Doc<"convexMembers">;
+    if (!member) {
+      throw new Error(`Member ${memberId} not found`);
+    }
+    if (!member.isDeletedAccount) {
+      throw new Error(`Member ${memberId} is not soft deleted`);
+    }
+    console.log(`Processing soft-deleted member ${memberId}`);
+    const sessions = await ctx.db
+      .query("sessions")
+      .withIndex("byMemberId", (q) => q.eq("memberId", memberId))
+      .collect();
+
+    if (sessions.length === 0) {
+      console.log(`No sessions found for member ${memberId}, deleting member data`);
+      const projectCredentials = await ctx.db
+        .query("convexProjectCredentials")
+        .withIndex("byMemberId", (q) => q.eq("memberId", memberId))
+        .collect();
+      for (const projectCredential of projectCredentials) {
+        await ctx.db.delete(projectCredential._id);
+      }
+      const openaiTokens = await ctx.db
+        .query("memberOpenAITokens")
+        .withIndex("byMemberId", (q) => q.eq("memberId", memberId))
+        .collect();
+      for (const openaiToken of openaiTokens) {
+        await ctx.db.delete(openaiToken._id);
+      }
+
+      const resendTokens = await ctx.db
+        .query("resendTokens")
+        .withIndex("byMemberId", (q) => q.eq("memberId", memberId))
+        .collect();
+      for (const resendToken of resendTokens) {
+        await ctx.db.delete(resendToken._id);
+      }
+
+      const convexAdmins = await ctx.db
+        .query("convexAdmins")
+        .withIndex("byConvexMemberId", (q) => q.eq("memberId", memberId))
+        .collect();
+      for (const convexAdmin of convexAdmins) {
+        await ctx.db.delete(convexAdmin._id);
+      }
+
+      await ctx.db.delete(memberId);
+      return;
+    }
+
+    for (const session of sessions) {
+      const chats = await ctx.db
+        .query("chats")
+        .withIndex("byCreatorAndId", (q) => q.eq("creatorId", session._id))
+        .collect();
+
+      if (chats.length === 0) {
+        console.log(`No chats found for session ${session._id}, deleting session`);
+        await ctx.db.delete(session._id);
+        return;
+      }
+
+      for (const chat of chats) {
+        ctx.scheduler.runAfter(calculateJitteredDelay(50, 0.2), internal.cleanup.deleteChat, {
+          chatId: chat._id,
+        });
+      }
+    }
+  },
+});
+
+export const deleteChat = internalMutation({
+  args: { chatId: v.id("chats") },
+  handler: async (ctx, { chatId }) => {
+    const chat: Doc<"chats"> = (await ctx.db.get(chatId)) as Doc<"chats">;
+    if (!chat) {
+      throw new Error(`Chat ${chatId} not found`);
+    }
+
+    const messages = await ctx.db
+      .query("chatMessagesStorageState")
+      .withIndex("byChatId", (q) => q.eq("chatId", chat._id))
+      .collect();
+
+    if (messages.length === 0) {
+      console.log(`No messages found for chat ${chat._id}, deleting chat`);
+      await ctx.db.delete(chat._id);
+      return;
+    }
+
+    const debugLogs = await ctx.db
+      .query("debugChatApiRequestLog")
+      .withIndex("byChatId", (q) => q.eq("chatId", chat._id))
+      .collect();
+
+    for (const log of debugLogs) {
+      await ctx.db.delete(log._id);
+    }
+
+    for (const message of messages) {
+      if (message.storageId) {
+        await ctx.storage.delete(message.storageId);
+      }
+      // also snapshot id
+      // also delete shares
+      await ctx.db.delete(message._id);
+    }
+  },
+});
+
+function calculateJitteredDelay(baseDelayMs: number, jitterFactor: number) {
+  // Generate a random number between -jitterFactor and +jitterFactor
+  const randomJitter = (Math.random() * 2 - 1) * jitterFactor;
+  // Apply the jitter to the base delay
+  return baseDelayMs * (1 + randomJitter);
+}
diff --git a/convex/crons.ts b/convex/crons.ts
index 04a6a0ef6..d05b0f319 100644
--- a/convex/crons.ts
+++ b/convex/crons.ts
@@ -10,4 +10,8 @@ crons.daily(
   { forReal: true, shouldScheduleNext: true, daysInactive: 14 },
 );
 
+crons.(
+  "delete inactive users and chats"
+)
+
 export default crons;
diff --git a/convex/schema.ts b/convex/schema.ts
index a7e593fb5..235299aed 100644
--- a/convex/schema.ts
+++ b/convex/schema.ts
@@ -40,6 +40,7 @@ export default defineSchema({
     apiKey: v.optional(apiKeyValidator),
     convexMemberId: v.optional(v.string()),
     softDeletedForWorkOSMerge: v.optional(v.boolean()),
+    isDeletedAccount: v.optional(v.boolean()),
     // Not authoritative, just a cache of the user's profile from WorkOS/provision host.
     cachedProfile: v.optional(
       v.object({
@@ -51,7 +52,8 @@ export default defineSchema({
     ),
   })
     .index("byTokenIdentifier", ["tokenIdentifier"])
-    .index("byConvexMemberId", ["convexMemberId", "softDeletedForWorkOSMerge"]),
+    .index("byConvexMemberId", ["convexMemberId", "softDeletedForWorkOSMerge"])
+    .index("byIsDeletedAccount", ["isDeletedAccount"]),
 
   /*
    * Admin status means being on the convex team on the provision host.
@@ -115,7 +117,9 @@ export default defineSchema({
     teamSlug: v.string(),
     memberId: v.optional(v.id("convexMembers")),
     projectDeployKey: v.string(),
-  }).index("bySlugs", ["teamSlug", "projectSlug"]),
+  })
+    .index("bySlugs", ["teamSlug", "projectSlug"])
+    .index("byMemberId", ["memberId"]),
   chatMessagesStorageState: defineTable({
     chatId: v.id("chats"),
     storageId: v.union(v.id("_storage"), v.null()),