diff --git a/lambda/workorder-sync/index.ts b/lambda/workorder-sync/index.ts
new file mode 100644
index 0000000..45100ab
--- /dev/null
+++ b/lambda/workorder-sync/index.ts
@@ -0,0 +1,268 @@
+import {
+  S3Client,
+  PutObjectCommand,
+  ListObjectsV2Command,
+  DeleteObjectsCommand,
+} from '@aws-sdk/client-s3';
+import {
+  DynamoDBClient,
+  ScanCommand,
+  QueryCommand,
+} from '@aws-sdk/client-dynamodb';
+import { unmarshall } from '@aws-sdk/util-dynamodb';
+import {
+  BedrockAgentClient,
+  StartIngestionJobCommand,
+} from '@aws-sdk/client-bedrock-agent';
+
+const s3 = new S3Client({});
+const dynamo = new DynamoDBClient({});
+const bedrockAgent = new BedrockAgentClient({ region: process.env.REGION! });
+
+const WO_PREFIX = 'work-orders/';
+
+interface WorkOrder {
+  work_order_id: string;
+  description?: string;
+  wo_status?: string;
+  customer?: string;
+  site_code?: string;
+  building?: string;
+  address?: string;
+  severity?: string;
+  priority?: string;
+  date_reported?: string;
+  scheduled_start?: string;
+  due_date?: string;
+  assigned_to?: string;
+  source_email_s3_key?: string;
+  created_at?: string;
+  updated_at?: string;
+  record_type?: string;
+}
+
+interface WorkOrderComment {
+  work_order_id: string;
+  comment_id: string;
+  record_type?: string;
+  commenter?: string;
+  text?: string;
+  created_at?: string;
+  source_email_s3_key?: string;
+  ingested_at?: string;
+}
+
+/** List all existing S3 keys under the work-orders/ prefix. */
+async function listExistingKeys(bucket: string): Promise<Set<string>> {
+  const keys = new Set<string>();
+  let continuationToken: string | undefined;
+
+  do {
+    const res = await s3.send(
+      new ListObjectsV2Command({
+        Bucket: bucket,
+        Prefix: WO_PREFIX,
+        ContinuationToken: continuationToken,
+      }),
+    );
+    for (const obj of res.Contents ?? []) {
+      if (obj.Key) keys.add(obj.Key);
+    }
+    continuationToken = res.NextContinuationToken;
+  } while (continuationToken);
+
+  return keys;
+}
+
+/** Delete S3 keys that no longer correspond to active records. */
+async function deleteStaleKeys(bucket: string, keys: string[]): Promise<void> {
+  if (keys.length === 0) return;
+
+  for (let i = 0; i < keys.length; i += 1000) {
+    await s3.send(
+      new DeleteObjectsCommand({
+        Bucket: bucket,
+        Delete: { Objects: keys.slice(i, i + 1000).map((Key) => ({ Key })) },
+      }),
+    );
+  }
+  console.log(`Deleted ${keys.length} stale work order file(s) from S3`);
+}
+
+async function scanAllWorkOrders(): Promise<WorkOrder[]> {
+  const results: WorkOrder[] = [];
+  let lastKey: Record<string, any> | undefined;
+
+  do {
+    const res = await dynamo.send(
+      new ScanCommand({
+        TableName: process.env.WORK_ORDERS_TABLE!,
+        ExclusiveStartKey: lastKey,
+      }),
+    );
+    for (const item of res.Items ?? []) {
+      results.push(unmarshall(item) as WorkOrder);
+    }
+    lastKey = res.LastEvaluatedKey;
+  } while (lastKey);
+
+  return results;
+}
+
+async function getComments(workOrderId: string): Promise<WorkOrderComment[]> {
+  const results: WorkOrderComment[] = [];
+  let lastKey: Record<string, any> | undefined;
+
+  do {
+    const res = await dynamo.send(
+      new QueryCommand({
+        TableName: process.env.COMMENTS_TABLE!,
+        KeyConditionExpression: 'work_order_id = :woid',
+        ExpressionAttributeValues: {
+          ':woid': { S: workOrderId },
+        },
+        ExclusiveStartKey: lastKey,
+      }),
+    );
+    for (const item of res.Items ?? []) {
+      results.push(unmarshall(item) as WorkOrderComment);
+    }
+    lastKey = res.LastEvaluatedKey;
+  } while (lastKey);
+
+  // Sort chronologically by created_at
+  results.sort((a, b) => (a.created_at ?? '').localeCompare(b.created_at ?? ''));
+
+  return results;
+}
+
+function formatWorkOrderMarkdown(wo: WorkOrder, comments: WorkOrderComment[]): string {
+  const lines: string[] = [];
+
+  lines.push(`# Work Order: ${wo.work_order_id}`);
+  lines.push('');
+
+  if (wo.description) {
+    lines.push(`## Description`);
+    lines.push('');
+    lines.push(wo.description);
+    lines.push('');
+  }
+
+  lines.push(`## Details`);
+  lines.push('');
+  lines.push(`| Field | Value |`);
+  lines.push(`| ----- | ----- |`);
+  if (wo.wo_status) lines.push(`| Status | ${wo.wo_status} |`);
+  if (wo.customer) lines.push(`| Customer | ${wo.customer} |`);
+  if (wo.site_code) lines.push(`| Site Code | ${wo.site_code} |`);
+  if (wo.building) lines.push(`| Building | ${wo.building} |`);
+  if (wo.address) lines.push(`| Address | ${wo.address} |`);
+  if (wo.severity) lines.push(`| Severity | ${wo.severity} |`);
+  if (wo.priority) lines.push(`| Priority | ${wo.priority} |`);
+  if (wo.assigned_to) lines.push(`| Assigned To | ${wo.assigned_to} |`);
+  if (wo.record_type) lines.push(`| Record Type | ${wo.record_type} |`);
+  lines.push('');
+
+  lines.push(`## Dates`);
+  lines.push('');
+  lines.push(`| Field | Value |`);
+  lines.push(`| ----- | ----- |`);
+  if (wo.date_reported) lines.push(`| Date Reported | ${wo.date_reported} |`);
+  if (wo.scheduled_start) lines.push(`| Scheduled Start | ${wo.scheduled_start} |`);
+  if (wo.due_date) lines.push(`| Due Date | ${wo.due_date} |`);
+  if (wo.created_at) lines.push(`| Created At | ${wo.created_at} |`);
+  if (wo.updated_at) lines.push(`| Updated At | ${wo.updated_at} |`);
+  lines.push('');
+
+  if (comments.length > 0) {
+    lines.push(`## Comment History`);
+    lines.push('');
+    for (const comment of comments) {
+      const timestamp = comment.created_at ?? 'unknown date';
+      const author = comment.commenter ?? 'unknown';
+      const type = comment.record_type ? ` [${comment.record_type}]` : '';
+      lines.push(`### ${timestamp} - ${author}${type}`);
+      lines.push('');
+      if (comment.text) {
+        lines.push(comment.text);
+        lines.push('');
+      }
+    }
+  }
+
+  return lines.join('\n');
+}
+
+export const handler = async (): Promise<void> => {
+  const bucket = process.env.KB_BUCKET_NAME!;
+  const kbId = process.env.KNOWLEDGE_BASE_ID!;
+  const dsId = process.env.DATA_SOURCE_ID!;
+
+  console.log('Listing existing work order files in S3...');
+  const existingKeys = await listExistingKeys(bucket);
+  console.log(`Found ${existingKeys.size} existing file(s) in S3`);
+
+  console.log('Scanning work orders from DynamoDB...');
+  const workOrders = await scanAllWorkOrders();
+  console.log(`Found ${workOrders.length} work order(s)`);
+
+  const writtenKeys = new Set<string>();
+  let synced = 0;
+  let failed = 0;
+
+  // Upload in batches of 10 (each WO also queries comments, so keep concurrency moderate)
+  const CONCURRENCY = 10;
+  for (let i = 0; i < workOrders.length; i += CONCURRENCY) {
+    const batch = workOrders.slice(i, i + CONCURRENCY);
+    const results = await Promise.allSettled(
+      batch.map(async (wo) => {
+        const comments = await getComments(wo.work_order_id);
+        const markdown = formatWorkOrderMarkdown(wo, comments);
+        const key = `${WO_PREFIX}${wo.work_order_id}.md`;
+
+        await s3.send(
+          new PutObjectCommand({
+            Bucket: bucket,
+            Key: key,
+            Body: markdown,
+            ContentType: 'text/markdown',
+            Metadata: {
+              'work-order-id': wo.work_order_id,
+              'site-code': (wo.site_code ?? '').slice(0, 256),
+            },
+          }),
+        );
+
+        return key;
+      }),
+    );
+
+    for (const r of results) {
+      if (r.status === 'fulfilled') {
+        writtenKeys.add(r.value);
+        synced++;
+      } else {
+        console.error(`Failed to sync work order:`, r.reason);
+        failed++;
+      }
+    }
+  }
+
+  console.log(`Upload complete. ${synced} synced, ${failed} failed.`);
+
+  // Delete S3 files for records that no longer exist in DynamoDB
+  const staleKeys = [...existingKeys].filter((k) => !writtenKeys.has(k));
+  await deleteStaleKeys(bucket, staleKeys);
+
+  console.log('Triggering Bedrock KB ingestion job...');
+  const ingestionRes = await bedrockAgent.send(
+    new StartIngestionJobCommand({
+      knowledgeBaseId: kbId,
+      dataSourceId: dsId,
+    }),
+  );
+  console.log(
+    `Ingestion job started: ${ingestionRes.ingestionJob?.ingestionJobId}`,
+  );
+};
diff --git a/lib/constructs/workorder-sync.ts b/lib/constructs/workorder-sync.ts
new file mode 100644
index 0000000..eb28fd5
--- /dev/null
+++ b/lib/constructs/workorder-sync.ts
@@ -0,0 +1,76 @@
+import * as cdk from 'aws-cdk-lib';
+import { Construct } from 'constructs';
+import * as lambda from 'aws-cdk-lib/aws-lambda';
+import * as lambdaNodejs from 'aws-cdk-lib/aws-lambda-nodejs';
+import * as s3 from 'aws-cdk-lib/aws-s3';
+import * as dynamodb from 'aws-cdk-lib/aws-dynamodb';
+import * as events from 'aws-cdk-lib/aws-events';
+import * as targets from 'aws-cdk-lib/aws-events-targets';
+import * as iam from 'aws-cdk-lib/aws-iam';
+import * as path from 'path';
+
+export interface WorkorderSyncProps {
+  region: string;
+  kbDocsBucket: s3.Bucket;
+  knowledgeBaseId: string;
+  dataSourceId: string;
+}
+
+export class WorkorderSyncConstruct extends Construct {
+  public readonly syncLambda: lambdaNodejs.NodejsFunction;
+
+  constructor(scope: Construct, id: string, props: WorkorderSyncProps) {
+    super(scope, id);
+
+    // Import existing DynamoDB tables by name (owned by workorder-ingest stack)
+    const workOrdersTable = dynamodb.Table.fromTableName(
+      this, 'WorkOrdersTable', 'WorkOrders',
+    );
+    const commentsTable = dynamodb.Table.fromTableName(
+      this, 'WorkOrderCommentsTable', 'WorkOrderComments',
+    );
+
+    // Lambda — scans DynamoDB work orders + comments, uploads markdown to S3, triggers KB ingestion
+    this.syncLambda = new lambdaNodejs.NodejsFunction(this, 'SyncLambda', {
+      functionName: 'seahaven-workorder-sync',
+      entry: path.join(__dirname, '../../lambda/workorder-sync/index.ts'),
+      runtime: lambda.Runtime.NODEJS_22_X,
+      memorySize: 512,
+      timeout: cdk.Duration.minutes(5),
+      environment: {
+        WORK_ORDERS_TABLE: workOrdersTable.tableName,
+        COMMENTS_TABLE: commentsTable.tableName,
+        KB_BUCKET_NAME: props.kbDocsBucket.bucketName,
+        KNOWLEDGE_BASE_ID: props.knowledgeBaseId,
+        DATA_SOURCE_ID: props.dataSourceId,
+        REGION: props.region,
+      },
+    });
+
+    // Grant read access to both DynamoDB tables
+    workOrdersTable.grantReadData(this.syncLambda);
+    commentsTable.grantReadData(this.syncLambda);
+
+    // Grant read/write to the KB docs bucket (read to list+delete old, write new)
+    props.kbDocsBucket.grantReadWrite(this.syncLambda);
+
+    // Allow Lambda to start a Bedrock KB ingestion job
+    this.syncLambda.addToRolePolicy(
+      new iam.PolicyStatement({
+        actions: ['bedrock:StartIngestionJob'],
+        resources: [
+          `arn:aws:bedrock:${props.region}:*:knowledge-base/${props.knowledgeBaseId}`,
+        ],
+      }),
+    );
+
+    // EventBridge rule — fires daily at 02:00 UTC
+    const dailyRule = new events.Rule(this, 'DailySyncRule', {
+      ruleName: 'seahaven-workorder-daily-sync',
+      description: 'Daily Work Orders → KB sync at 02:00 UTC',
+      schedule: events.Schedule.cron({ minute: '0', hour: '2' }),
+    });
+
+    dailyRule.addTarget(new targets.LambdaFunction(this.syncLambda));
+  }
+}
diff --git a/lib/seahaven-slack-bot-stack.ts b/lib/seahaven-slack-bot-stack.ts
index daa0d82..d7814f2 100644
--- a/lib/seahaven-slack-bot-stack.ts
+++ b/lib/seahaven-slack-bot-stack.ts
@@ -6,6 +6,7 @@ import { BedrockAgentConstruct } from './constructs/bedrock-agent';
 import { SlackHandlerConstruct } from './constructs/slack-handler';
 import { NotionSyncConstruct } from './constructs/notion-sync';
 import { PoSyncConstruct } from './constructs/po-sync';
+import { WorkorderSyncConstruct } from './constructs/workorder-sync';
 
 export class SeahavenSlackBotStack extends cdk.Stack {
   constructor(scope: Construct, id: string, props?: cdk.StackProps) {
@@ -53,6 +54,14 @@ export class SeahavenSlackBotStack extends cdk.Stack {
       dataSourceId: knowledgeBase.dataSource.dataSourceId,
     });
 
+    // ── Work Orders → KB daily sync (EventBridge + Lambda) ────────────────────
+    new WorkorderSyncConstruct(this, 'WorkorderSync', {
+      region: this.region,
+      kbDocsBucket: knowledgeBase.docsBucket,
+      knowledgeBaseId: knowledgeBase.knowledgeBase.knowledgeBaseId,
+      dataSourceId: knowledgeBase.dataSource.dataSourceId,
+    });
+
     // ── Slack webhook handler (API Gateway + Lambda) ───────────────────────────
     new SlackHandlerConstruct(this, 'SlackHandler', {
       accountId: this.account,