diff --git a/api/src/services/notifications.ts b/api/src/services/notifications.ts
index f01cde9b..a0e5ff76 100644
--- a/api/src/services/notifications.ts
+++ b/api/src/services/notifications.ts
@@ -108,12 +108,16 @@ export const NOTIFICATION_KINDS = {
   }),
   work_order_accepted: (p) => ({
     title: `${p.builderName} signed Work Order ${p.code}`,
-    body: `${p.builderName} signed Work Order ${p.code} on ${p.projectTitle}. Countersign it on MultiAgency, then activate it to start the work period.`,
+    body: `${p.builderName} signed Work Order ${p.code} on ${p.projectTitle}. It starts on its own once both of you have signed and nothing else blocks it.`,
   }),
   work_order_declined: (p) => ({
     title: `${p.builderName} declined Work Order ${p.code}`,
     body: `${p.builderName} declined Work Order ${p.code} on ${p.projectTitle}${p.note ? `: ${p.note}` : "."} It is back in draft.`,
   }),
+  work_order_esign_cancelled: (p) => ({
+    title: `The signing request for Work Order ${p.code} was cancelled`,
+    body: `The signing request for Work Order ${p.code} on ${p.projectTitle} was cancelled, so it is back in draft.`,
+  }),
   work_order_signed: (p) => ({
     title: `Work Order ${p.code} is signed`,
     body: `Work Order ${p.code} on ${p.projectTitle} was signed by both parties. It starts automatically once nothing else blocks it.`,
@@ -132,7 +136,7 @@ export const NOTIFICATION_KINDS = {
   }),
   work_order_payee_confirmed: (p) => ({
     title: `${p.builderName} confirmed the payout account for ${p.code}`,
-    body: `${p.builderName} proved they control the payout account of Work Order ${p.code} on ${p.projectTitle}. You can activate it.`,
+    body: `${p.builderName} proved they control the payout account of Work Order ${p.code} on ${p.projectTitle}. It starts on its own unless something else blocks it.`,
   }),
   work_order_activated: (p) => ({
     title: `Work Order ${p.code} is active`,
@@ -198,6 +202,14 @@ export const NOTIFICATION_KINDS = {
     title: `Renewal of ${p.code} needs your decision`,
     body: `Work Order ${p.code} on ${p.projectTitle} missed ${p.missed} for renewal. Renew it anyway or let it end on MultiAgency.`,
   }),
+  work_order_terminated: (p) => ({
+    title: `${p.agencyName} ended Work Order ${p.code}`,
+    body: `${p.agencyName} terminated Work Order ${p.code} on ${p.projectTitle}. You can't send new payout requests under it; payouts already sent aren't affected.`,
+  }),
+  work_order_withdrawn: (p) => ({
+    title: `${p.agencyName} withdrew Work Order ${p.code}`,
+    body: `${p.agencyName} withdrew the offer of Work Order ${p.code} on ${p.projectTitle}, so there's nothing to sign. If you got a signing link for it, ignore it.`,
+  }),
   work_order_not_renewed: (p) => ({
     title: `Work Order ${p.code} is not renewed`,
     body: `Work Order ${p.code} on ${p.projectTitle} ends with this period.`,
diff --git a/api/src/services/work-orders/emails.ts b/api/src/services/work-orders/emails.ts
index 3662a949..00bed077 100644
--- a/api/src/services/work-orders/emails.ts
+++ b/api/src/services/work-orders/emails.ts
@@ -71,6 +71,10 @@ export function composeEmails(e: WorkOrderEvent): WorkOrderEmail[] {
     return url ? { label, url } : null;
   };
 
+  const starts = wo.periodStarted
+    ? "it starts right away"
+    : `its work period runs from ${wo.periodStart} to ${wo.periodEnd}`;
+
   const send = (role: Role, subject: string, draft: Draft) => {
     const person = role === "contractor" ? e.contractor : e.representative;
     if (!person.email) return;
@@ -83,13 +87,13 @@ export function composeEmails(e: WorkOrderEvent): WorkOrderEmail[] {
     case "work_order.offered":
       send("contractor", `${agency} sent you Work Order ${wo.id} to sign`, {
         preheader: e.links.sign
-          ? `${agency} has signed ${wo.title}. Sign it to accept; it starts right away.`
+          ? `${agency} has signed ${wo.title}. Sign it to accept; ${starts}.`
           : `${wo.title}: review the terms and sign to accept.`,
         eyebrow: "Work order sent",
         heading: `${agency} sent you a work order`,
         paragraphs: [
           e.links.sign
-            ? `You're offered "${wo.title}" on ${wo.project}, and ${agency} has already signed it. Review the terms and sign to accept. As soon as you sign, it's complete and starts right away.`
+            ? `You're offered "${wo.title}" on ${wo.project}, and ${agency} has already signed it. Review the terms and sign to accept. As soon as you sign, it's complete: ${starts}.`
             : `You're offered "${wo.title}" on ${wo.project}. Review the terms and sign to accept. It only takes a minute.`,
           `Each approved payout request is paid to ${e.contractor.nearAccount}.`,
         ],
@@ -129,7 +133,7 @@ export function composeEmails(e: WorkOrderEvent): WorkOrderEmail[] {
         heading: `Work Order ${wo.id} is signed`,
         paragraphs: [
           `${builder} and ${agency} have both signed. The signed PDF is attached to the work order.`,
-          "It becomes active automatically when its period starts.",
+          "It starts on its own unless something still blocks it, such as a payout account to confirm. The work order shows anything that's left.",
         ],
         details: summary(["Builder", builder], ["Budget", wo.budget]),
         action: view("representative"),
@@ -138,17 +142,157 @@ export function composeEmails(e: WorkOrderEvent): WorkOrderEmail[] {
           : [],
       });
       break;
-    case "work_order.active":
+    case "work_order.active": {
+      const upcoming = !wo.periodStarted;
       send("contractor", `Work Order ${wo.id} is active`, {
-        preheader: `Your work period has started: ${period}.`,
+        preheader: upcoming
+          ? `Your work period starts on ${wo.periodStart}: ${period}.`
+          : `Your work period has started: ${period}.`,
         eyebrow: "Work order active",
         heading: `Work Order ${wo.id} is active`,
-        paragraphs: ["Your work period has started. Here's how your work is counted:"],
+        paragraphs: [
+          upcoming
+            ? `Your work period starts on ${wo.periodStart}. Here's how your work is counted:`
+            : "Your work period has started. Here's how your work is counted:",
+        ],
         list: { title: null, items: COUNTING_RULES },
         details: summary(["Budget", wo.budget], ["Paid to", e.contractor.nearAccount]),
         action: view("contractor"),
       });
       break;
+    }
+    case "work_order.sign_first":
+      send("representative", `Sign Work Order ${wo.id} to send it to ${builder}`, {
+        preheader: `${builder} gets their signing link as soon as you've signed.`,
+        eyebrow: "Your signature needed",
+        heading: `Sign Work Order ${wo.id} first`,
+        paragraphs: [
+          `"${wo.title}" for ${builder} is ready in Documenso. You sign first for ${agency}; ${builder} gets their signing link as soon as you have.`,
+          "Until you sign, nothing has gone to the builder.",
+        ],
+        details: summary(["Builder", builder], ["Budget", `up to ${wo.budget}`]),
+        action: e.links.countersign
+          ? { label: "Review and sign", url: e.links.countersign }
+          : view("representative", "Open the work order"),
+        secondary:
+          e.links.countersign && e.links.review
+            ? [{ label: "View it on MultiAgency", url: e.links.review }]
+            : [],
+      });
+      break;
+    case "work_order.declined":
+      send("representative", `${builder} declined Work Order ${wo.id}`, {
+        preheader: `${wo.title} is back in draft.`,
+        eyebrow: "Work order declined",
+        heading: `${builder} declined Work Order ${wo.id}`,
+        paragraphs: [
+          `${builder} declined "${wo.title}". It's back in draft: edit it and send it again, or delete it.`,
+          ...(e.note ? [`Their note: "${e.note}"`] : []),
+        ],
+        details: summary(["Builder", builder], ["Budget", wo.budget]),
+        action: view("representative"),
+      });
+      break;
+    case "work_order.esign_cancelled":
+      send("representative", `The signing request for Work Order ${wo.id} was cancelled`, {
+        preheader: `${wo.title} is back in draft.`,
+        eyebrow: "Signing cancelled",
+        heading: `The signing request for Work Order ${wo.id} was cancelled`,
+        paragraphs: [
+          `The signing request for "${wo.title}" was cancelled, so it's back in draft. Send it again, or delete it.`,
+        ],
+        details: summary(["Builder", builder], ["Budget", wo.budget]),
+        action: view("representative"),
+      });
+      break;
+    case "work_order.confirm_payee":
+      send("contractor", `Confirm your payout account for Work Order ${wo.id}`, {
+        preheader: `Confirm ${e.contractor.nearAccount} so you can be paid.`,
+        eyebrow: "Payout account",
+        heading: "Confirm your payout account",
+        paragraphs: [
+          `${agency} hasn't paid ${e.contractor.nearAccount} before. Open the work order signed in with that NEAR account and confirm it.`,
+          "It's free, takes a few seconds and doesn't move any money.",
+        ],
+        details: summary(["Paid to", e.contractor.nearAccount]),
+        action: e.links.confirm
+          ? { label: "Confirm the account", url: e.links.confirm }
+          : view("contractor", "Confirm the account"),
+      });
+      break;
+    case "work_order.ending_soon":
+      send("contractor", `Work Order ${wo.id} ends on ${wo.periodEnd}`, {
+        preheader: `Your work period ends on ${wo.periodEnd}.`,
+        eyebrow: "Ending soon",
+        heading: `Your work period ends on ${wo.periodEnd}`,
+        paragraphs: [
+          "Your report and payout request are drafted right after it ends; you review them and send the request.",
+          'Make sure your pull requests close their assigned issues ("Closes #12") so they count.',
+        ],
+        details: summary(["Budget", wo.budget]),
+        action: view("contractor"),
+      });
+      break;
+    case "work_order.renewal_needs_approval": {
+      const metrics = e.renewal?.assessment.metrics ?? [];
+      send("representative", `Renew ${builder}'s Work Order ${wo.id}? It needs your decision`, {
+        preheader: `It missed a renewal target, so it wasn't renewed automatically.`,
+        eyebrow: "Renewal needs a decision",
+        heading: `Renew ${builder}'s work order?`,
+        paragraphs: [
+          `The period of "${wo.title}" is over and it missed at least one renewal target, so it wasn't renewed automatically. Renew it anyway or let it end.`,
+        ],
+        list: metrics.length
+          ? {
+              title: "Renewal targets",
+              items: metrics.map(
+                (m) => `${m.met ? "Met" : "Missed"}: ${m.label}: ${m.value} (needs ${m.target})`,
+              ),
+            }
+          : undefined,
+        details: summary(["Builder", builder], ["Budget", wo.budget]),
+        action: view("representative", "Decide on the renewal"),
+      });
+      break;
+    }
+    case "work_order.not_renewed":
+      send("contractor", `Work Order ${wo.id} isn't renewed`, {
+        preheader: `${wo.title} ends with this period.`,
+        eyebrow: "Not renewed",
+        heading: `Work Order ${wo.id} isn't renewed`,
+        paragraphs: [
+          `${agency} didn't renew "${wo.title}". It ends with this period.`,
+          "Payout requests for work done in this period still go through as usual.",
+        ],
+        details: summary(["Budget", wo.budget]),
+        action: view("contractor"),
+      });
+      break;
+    case "work_order.terminated":
+      send("contractor", `${agency} ended Work Order ${wo.id}`, {
+        preheader: `${wo.title} is terminated.`,
+        eyebrow: "Work order ended",
+        heading: `${agency} ended Work Order ${wo.id}`,
+        paragraphs: [
+          `${agency} terminated "${wo.title}". You can't send new payout requests under it.`,
+          `Payouts already sent aren't affected. Contact ${agency} if you have questions.`,
+        ],
+        details: summary(["Budget", wo.budget]),
+        action: view("contractor"),
+      });
+      break;
+    case "work_order.withdrawn":
+      send("contractor", `${agency} withdrew Work Order ${wo.id}`, {
+        preheader: `There's nothing to sign: ${wo.title} was withdrawn.`,
+        eyebrow: "Work order withdrawn",
+        heading: `${agency} withdrew Work Order ${wo.id}`,
+        paragraphs: [
+          `${agency} withdrew its offer of "${wo.title}", so there's nothing to sign. If you got a signing link for it, ignore it.`,
+          `Contact ${agency} if you have questions.`,
+        ],
+        details: summary(["Budget", `up to ${wo.budget}`]),
+      });
+      break;
     case "work_order.renewed": {
       const unsent = e.renewal?.unsent ?? null;
       const signLink = unsent ? null : (e.links.countersign ?? null);
@@ -185,6 +329,20 @@ export function composeEmails(e: WorkOrderEvent): WorkOrderEmail[] {
       });
       break;
     }
+    case "request.report_ready":
+      send("contractor", `Your report for Work Order ${wo.id} is ready to send`, {
+        preheader: `Review your report and send your payout request${r?.requested ? ` for ${r.requested}` : ""}.`,
+        eyebrow: "Report ready",
+        heading: "Your report is ready to review",
+        paragraphs: [
+          `Payout request ${r?.id ?? ""} was drafted from your GitHub activity. Review the report, add any work outside GitHub and send it to ${agency}.`,
+          "You're only paid once you send it.",
+        ],
+        details: summary(["Request", r?.id ?? ""], ["Requested", r?.requested ?? ""]),
+        action: view("contractor", "Review and send"),
+        block: e.reportMd ? { title: "Draft report", body: e.reportMd } : null,
+      });
+      break;
     case "request.awaiting_approval":
       send("contractor", `Your payout request for ${wo.id} was sent`, {
         preheader: `${r?.requested ?? "Your request"} is waiting for ${agency}'s approval.`,
diff --git a/api/src/services/work-orders/events.ts b/api/src/services/work-orders/events.ts
index 0c31b4b0..c5fa7360 100644
--- a/api/src/services/work-orders/events.ts
+++ b/api/src/services/work-orders/events.ts
@@ -4,16 +4,20 @@ export const WORK_ORDER_EVENT_TYPES = [
   "work_order.created",
   "work_order.signature_mismatch",
   "work_order.offered",
+  "work_order.sign_first",
   "work_order.builder_signed",
   "work_order.signed",
   "work_order.confirm_payee",
   "work_order.payee_confirmed",
   "work_order.active",
   "work_order.declined",
+  "work_order.esign_cancelled",
   "work_order.ending_soon",
   "work_order.renewed",
   "work_order.renewal_needs_approval",
   "work_order.not_renewed",
+  "work_order.terminated",
+  "work_order.withdrawn",
   "request.report_ready",
   "request.awaiting_approval",
   "request.approved",
@@ -50,6 +54,7 @@ export type WorkOrderEvent = {
     project: string;
     periodStart: string;
     periodEnd: string;
+    periodStarted: boolean;
     budget: string;
   };
   contractor: { name: string; email: string | null; github: string; nearAccount: string };
diff --git a/api/src/services/work-orders/service.ts b/api/src/services/work-orders/service.ts
index 0e15c119..746fb078 100644
--- a/api/src/services/work-orders/service.ts
+++ b/api/src/services/work-orders/service.ts
@@ -211,6 +211,7 @@ export type WorkOrderFields = {
 type WorkOrderStatus = WorkOrderRow["status"];
 type RequestStatus = CompensationRequestRow["status"];
 type PendingEnvelope = { esign: EsignPort; envelopeId: string };
+type RequestDrafter = "schedule" | "agency" | "builder";
 type GoogleTemplate = {
   google: GooglePort;
   templateId: string;
@@ -506,13 +507,27 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
   async function contactsOf(row: WorkOrderRow, builder: BuilderProfile | null) {
     const lookup = async (userId: string | null | undefined) =>
       userId && deps.userEmail ? await deps.userEmail(userId).catch(() => null) : null;
+    const fallback = row.representativeEmail
+      ? null
+      : await integrationOf(row.organizationId).catch(() => null);
+    const useDefault = !!fallback?.defaultRepresentativeEmail;
     return {
       contractorEmail: row.contractorEmail ?? (await lookup(builder?.userId)),
-      representativeEmail: row.representativeEmail,
+      representativeEmail: useDefault
+        ? (fallback?.defaultRepresentativeEmail ?? null)
+        : row.representativeEmail,
+      representativeName: useDefault
+        ? (fallback?.defaultRepresentativeName ?? null)
+        : row.representativeName,
     };
   }
 
-  async function announce(row: WorkOrderRow, type: WorkOrderEventType, extra: Announcement = {}) {
+  async function announce(
+    row: WorkOrderRow,
+    type: WorkOrderEventType,
+    extra: Announcement = {},
+    workOrderId: string | null = row.id,
+  ) {
     if (!deps.outbox) return;
     try {
       const [project, agencyName, builder] = await Promise.all([
@@ -534,6 +549,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
           project: project?.title ?? UNKNOWN_PROJECT,
           periodStart: row.periodStart,
           periodEnd: row.periodEnd,
+          periodStarted: today() >= row.periodStart,
           budget: display(row.budgetAmount, row.tokenId),
         },
         contractor: {
@@ -543,7 +559,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
           nearAccount: row.builderNearAccount,
         },
         representative: {
-          name: row.representativeName ?? agencyName,
+          name: contacts.representativeName ?? agencyName,
           email: contacts.representativeEmail,
         },
         request: request
@@ -597,7 +613,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         renewal: extra.renewal ?? null,
         hold: extra.hold ?? null,
       };
-      await deps.outbox.enqueue(row.organizationId, row.id, event);
+      await deps.outbox.enqueue(row.organizationId, workOrderId, event);
     } catch (error) {
       console.warn(`[API] work order ${row.code} ${type} couldn't be queued`, error);
     }
@@ -683,7 +699,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
       project: projectTitle,
       contractorName: row.contractorName ?? builder?.name ?? row.builderNearAccount,
       contractorEmail: contacts.contractorEmail,
-      representativeName: row.representativeName ?? agencyName,
+      representativeName: contacts.representativeName ?? agencyName,
       representativeEmail: contacts.representativeEmail,
       periodStart: row.periodStart,
       periodEnd: row.periodEnd,
@@ -896,7 +912,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
       ["Project", projectTitle],
       ["Builder (contractor)", row.contractorName ?? builder?.name ?? row.builderNearAccount],
       ["Builder's email", contacts.contractorEmail ?? ""],
-      ["Agency representative", row.representativeName ?? agencyName],
+      ["Agency representative", contacts.representativeName ?? agencyName],
       ["Representative's email", contacts.representativeEmail ?? ""],
       ["Work period", `${longDate(row.periodStart)} to ${longDate(row.periodEnd)}`],
       [
@@ -1376,6 +1392,15 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     };
   }
 
+  async function sentToBuilder(row: WorkOrderRow, state?: EsignStatus | null): Promise<boolean> {
+    if (row.status === "draft") return false;
+    if (row.status !== "offered") return true;
+    if (!(await signingOf(row)).awaitingRepresentative) return true;
+    const current =
+      state === undefined ? (await checkEnvelope(row).catch(() => null))?.state : state;
+    return !!current?.signers.some((s) => s.role === "representative" && s.signedAt);
+  }
+
   async function syncPendingSignatures(): Promise<number> {
     if (!deps.esign) return 0;
     const pending = await db
@@ -1411,7 +1436,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     const signers = [
       {
         role: "representative" as const,
-        name: row.representativeName ?? agencyName,
+        name: contacts.representativeName ?? agencyName,
         email: contacts.representativeEmail ?? "",
       },
       {
@@ -1545,20 +1570,29 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     let current = row.esignError ? await update(row.id, { esignError: null }) : row;
     if (state.status === "rejected") {
       if (current.status !== "offered") return current;
-      const reason = state.signers.find((s) => s.rejected)?.rejectionReason ?? "";
+      const rejecter = state.signers.find((s) => s.rejected);
+      const reason = rejecter?.rejectionReason ?? "";
       const declined = await update(row.id, {
         status: "draft",
         offeredAt: null,
         esignEnvelopeId: null,
         esignBuilderUrl: null,
         esignRepresentativeUrl: null,
-        esignError: `Declined in Documenso${reason ? `: ${reason}` : ""}`,
+        esignError: rejecter
+          ? `Declined in Documenso${reason ? `: ${reason}` : ""}`
+          : "Cancelled in Documenso",
       });
-      await notifyManagers(
-        declined,
-        "work_order_declined",
-        await payloadOf(declined, { note: reason }),
-      );
+      if (rejecter?.role === "contractor") {
+        await notifyManagers(
+          declined,
+          "work_order_declined",
+          await payloadOf(declined, { note: reason }),
+        );
+        await announce(declined, "work_order.declined", { note: reason || null });
+      } else if (!rejecter) {
+        await notifyManagers(declined, "work_order_esign_cancelled", await payloadOf(declined));
+        await announce(declined, "work_order.esign_cancelled");
+      }
       return declined;
     }
     const existing = await signaturesOf(row.id, offered.sha256);
@@ -2157,6 +2191,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     row: WorkOrderRow,
     kind: NotificationKind,
     payload: Record<string, string>,
+    link = builderLink(row.id),
   ) {
     const builder = await deps.builders.get(row.builderNearAccount).catch(() => null);
     if (!builder?.userId) return;
@@ -2166,7 +2201,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         organizationId: row.organizationId,
         kind,
         payload,
-        link: builderLink(row.id),
+        link,
       })
       .catch((error: unknown) => console.warn("[API] work order notification failed:", error));
   }
@@ -2459,7 +2494,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
   async function draftRequest(
     initial: WorkOrderRow,
     input: { coversFrom?: string; coversTo?: string },
-    auto = false,
+    drafter: RequestDrafter,
   ): Promise<CompensationRequestRow> {
     let row = initial;
     if (row.status !== "active" && row.status !== "ended") {
@@ -2477,7 +2512,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     if (amountsOf(row, existing).remaining <= 0n) {
       throw badRequest("BUDGET_USED", "The work order budget is used up");
     }
-    if (!auto) {
+    if (drafter !== "schedule") {
       try {
         row = await collect(row);
       } catch (error) {
@@ -2525,16 +2560,18 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         updatedAt: now(),
       })
       .returning();
-    if (auto) await update(row.id, { autoDraftedFor: row.periodEnd });
-    await notifyBuilder(
-      row,
-      "compensation_request_ready",
-      await payloadOf(row, { requestCode: `${row.code}-R${seq}` }),
-    );
-    await announce(row, "request.report_ready", {
-      request: inserted,
-      reportMd: draftReportOf(contributionsMd, assessmentMd),
-    });
+    if (drafter === "schedule") await update(row.id, { autoDraftedFor: row.periodEnd });
+    if (drafter !== "builder") {
+      await notifyBuilder(
+        row,
+        "compensation_request_ready",
+        await payloadOf(row, { requestCode: `${row.code}-R${seq}` }),
+      );
+      await announce(row, "request.report_ready", {
+        request: inserted,
+        reportMd: draftReportOf(contributionsMd, assessmentMd),
+      });
+    }
     return inserted!;
   }
 
@@ -3279,7 +3316,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     if (current.status === "ended" && current.autoDraftedFor !== current.periodEnd && !open) {
       const { remaining } = amountsOf(current, await requestsOf(current.id));
       if (remaining > 0n) {
-        await draftRequest(current, {}, true);
+        await draftRequest(current, {}, "schedule");
         counts.drafted = (counts.drafted ?? 0) + 1;
       } else {
         current = await update(current.id, { autoDraftedFor: current.periodEnd });
@@ -3795,6 +3832,12 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
           "Offer the work order or have it signed before asking for the payout account",
         );
       }
+      if (row.status === "offered" && row.esignEnvelopeId) {
+        throw badRequest(
+          "CONFIRMED_BY_SIGNING",
+          `The builder confirms ${row.builderNearAccount} by signing ${row.code} in Documenso`,
+        );
+      }
       await announce(row, "work_order.confirm_payee");
       await notifyBuilder(row, "work_order_confirm_payee", await payloadOf(row));
       return adminView(await view(row));
@@ -3807,6 +3850,8 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         if (!offered.esignEnvelopeId) {
           await notifyBuilder(offered, "work_order_offered", await payloadOf(offered));
           await announce(offered, "work_order.offered");
+        } else if ((await signingOf(offered)).awaitingRepresentative) {
+          await announce(offered, "work_order.sign_first");
         }
         return adminView(await view(offered));
       });
@@ -3846,7 +3891,6 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
       if (signatures.some((s) => s.role === "representative")) {
         throw badRequest("ALREADY_SIGNED", "You've already countersigned it");
       }
-      const contacts = await contactsOf(row, null);
       await db.insert(workOrderSignatures).values({
         id: crypto.randomUUID(),
         workOrderId: row.id,
@@ -3854,7 +3898,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         role: "representative",
         name,
         email:
-          contacts.representativeEmail ??
+          row.representativeEmail ??
           (deps.userEmail ? await deps.userEmail(scope.actorId).catch(() => null) : null),
         userId: scope.actorId,
         nearAccount: null,
@@ -3904,6 +3948,8 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         const row = await ownRow(scope, input.id);
         if (FINAL.includes(row.status))
           throw badRequest("CLOSED", `Work order ${row.code} is already terminated`);
+        const builderWasSent = await sentToBuilder(row);
+        const withdrawsOffer = row.status === "offered";
         const failed = await cancelEnvelope(row, "The work order was terminated");
         const terminated = await update(row.id, {
           status: "terminated",
@@ -3913,6 +3959,13 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
               }
             : {}),
         });
+        if (builderWasSent && withdrawsOffer) {
+          await notifyBuilder(terminated, "work_order_withdrawn", await payloadOf(terminated));
+          await announce(terminated, "work_order.withdrawn");
+        } else if (builderWasSent) {
+          await notifyBuilder(terminated, "work_order_terminated", await payloadOf(terminated));
+          await announce(terminated, "work_order.terminated");
+        }
         return adminView(await view(terminated));
       });
     },
@@ -3952,7 +4005,16 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
             );
           }
         }
+        const builderWasSent =
+          row.status === "offered" &&
+          checked?.state.status !== "rejected" &&
+          (await sentToBuilder(row, checked?.state ?? null));
+        const payload = builderWasSent ? await payloadOf(row) : null;
         await db.delete(workOrders).where(eq(workOrders.id, row.id));
+        if (payload) {
+          await notifyBuilder(row, "work_order_withdrawn", payload, "/dashboard");
+          await announce(row, "work_order.withdrawn", {}, null);
+        }
         return { deleted: true as const };
       });
     },
@@ -3965,7 +4027,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
       input: { id: string; coversFrom?: string; coversTo?: string },
     ) => {
       const row = await ownRow(scope, input.id);
-      return requestView(await draftRequest(row, input), row);
+      return requestView(await draftRequest(row, input, "agency"), row);
     },
 
     approveRequest: async (
@@ -4456,7 +4518,7 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
         throw badRequest(
           "SIGN_IN_DOCUMENSO",
           (await signingOf(row)).awaitingRepresentative
-            ? `Work order ${row.code} isn't ready for your signature yet: ${row.representativeName ?? "the agency"} signs it first`
+            ? `Work order ${row.code} isn't ready for your signature yet: ${(await contactsOf(row, null)).representativeName ?? "the agency"} signs it first`
             : `Sign work order ${row.code} with the Documenso link in your email or on the work order page`,
         );
       }
@@ -4569,7 +4631,10 @@ export function createWorkOrdersService(deps: WorkOrderDeps) {
     ) => {
       const row = await mustRow(input.id);
       requireBuilder(context, row);
-      return { ...(await requestView(await draftRequest(row, input), row)), trust: null };
+      return {
+        ...(await requestView(await draftRequest(row, input, "builder"), row)),
+        trust: null,
+      };
     },
 
     editRequest: async (
diff --git a/api/tests/integration/work-order-outbox.test.ts b/api/tests/integration/work-order-outbox.test.ts
index 96f8abc2..903f50b0 100644
--- a/api/tests/integration/work-order-outbox.test.ts
+++ b/api/tests/integration/work-order-outbox.test.ts
@@ -29,6 +29,7 @@ function event(type: WorkOrderEvent["type"], over: Partial<WorkOrderEvent> = {})
       project: "Search",
       periodStart: "2026-09-01",
       periodEnd: "2026-09-30",
+      periodStarted: true,
       budget: "1000 USDC",
     },
     contractor: {
@@ -80,12 +81,20 @@ describe("work order emails", () => {
     expect(to("request.awaiting_approval")).toEqual(["carol@example.com", "rita@example.com"]);
     expect(to("work_order.builder_signed")).toEqual(["rita@example.com"]);
     expect(to("request.approved")).toEqual(["carol@example.com"]);
-    for (const quiet of [
-      "work_order.created",
-      "work_order.confirm_payee",
-      "work_order.declined",
+    expect(to("work_order.sign_first")).toEqual(["rita@example.com"]);
+    expect(to("work_order.declined")).toEqual(["rita@example.com"]);
+    expect(to("work_order.renewal_needs_approval")).toEqual(["rita@example.com"]);
+    for (const builder of [
       "request.report_ready",
+      "work_order.confirm_payee",
+      "work_order.ending_soon",
+      "work_order.not_renewed",
+      "work_order.terminated",
+      "work_order.withdrawn",
     ] as const) {
+      expect(to(builder)).toEqual(["carol@example.com"]);
+    }
+    for (const quiet of ["work_order.created", "work_order.payee_confirmed"] as const) {
       expect(to(quiet)).toEqual([]);
     }
     const request = {
@@ -171,6 +180,43 @@ describe("work order emails", () => {
     expect(email?.html).toContain('href="https://sign.example/envelope_1/representative"');
   });
 
+  test("the representative is asked to sign a new Documenso order first", () => {
+    const base = event("work_order.sign_first");
+    const [email] = composeEmails(
+      event("work_order.sign_first", {
+        links: { ...base.links, countersign: "https://sign.example/envelope_1/representative" },
+      }),
+    );
+    expect(email?.subject).toBe("Sign Work Order SI-004 to send it to Carol");
+    expect(email?.html).toContain('href="https://sign.example/envelope_1/representative"');
+  });
+
+  test("signed and active emails say when the work order starts", () => {
+    const [signed] = composeEmails(event("work_order.signed"));
+    expect(signed?.text).not.toContain("when its period starts");
+    expect(signed?.text).toContain("starts on its own unless something still blocks it");
+    const [started] = composeEmails(event("work_order.active"));
+    expect(started?.text).toContain("Your work period has started");
+    const later = event("work_order.active");
+    later.workOrder.periodStarted = false;
+    const [upcoming] = composeEmails(later);
+    expect(upcoming?.text).toContain("Your work period starts on 2026-09-01");
+    expect(upcoming?.text).not.toContain("has started");
+    const offer = event("work_order.offered");
+    offer.links.sign = "https://sign.example/c";
+    offer.workOrder.periodStarted = false;
+    const [offered] = composeEmails(offer);
+    expect(offered?.text).toContain("its work period runs from 2026-09-01 to 2026-09-30");
+    expect(offered?.text).not.toContain("starts right away");
+  });
+
+  test("a withdrawn order tells the builder to ignore any signing link", () => {
+    const [email] = composeEmails(event("work_order.withdrawn"));
+    expect(email?.subject).toBe("Studio withdrew Work Order SI-004");
+    expect(email?.text).toContain("If you got a signing link for it, ignore it");
+    expect(email?.html).not.toContain("https://app.example/work-orders/1");
+  });
+
   test("emails go out once through Resend", async () => {
     const signed = event("work_order.signed");
     signed.links.document = "https://drive.example/signed?id=1&v=2";
diff --git a/api/tests/integration/work-orders.test.ts b/api/tests/integration/work-orders.test.ts
index c27ce0d4..209b1a25 100644
--- a/api/tests/integration/work-orders.test.ts
+++ b/api/tests/integration/work-orders.test.ts
@@ -12,6 +12,7 @@ import {
   workOrderDriveFiles,
   workOrderIntegrations,
   workOrderOutbox,
+  workOrderSignatures,
   workOrders,
 } from "../../src/db/schema";
 import { rememberedLogin } from "../../src/services/builder-logins";
@@ -961,10 +962,87 @@ describe("work orders", () => {
       expect(event?.links.review).toBe(`https://app.example/admin/work-orders/${created.id}`);
     });
 
-    test("agency emails go only to the representative's email on the work order", async () => {
+    test("agency emails go to the work order's representative, else the Agency's default one", async () => {
       await service.create(await studio(), fields({ tokenId: REAL_USDC }));
-      const event = events.find((e) => e.type === "work_order.created");
-      expect(event?.representative.email).toBeNull();
+      expect(events.find((e) => e.type === "work_order.created")?.representative.email).toBeNull();
+
+      await createWorkOrderIntegrations({ db }).saveRepresentative("studio", "studio-admin", {
+        name: "Dana Default",
+        email: "dana@example.com",
+      });
+      events.length = 0;
+      await service.create(await studio(), fields({ tokenId: REAL_USDC }));
+      expect(events.find((e) => e.type === "work_order.created")?.representative).toEqual({
+        name: "Dana Default",
+        email: "dana@example.com",
+      });
+
+      events.length = 0;
+      await service.create(
+        await studio(),
+        fields({ representativeName: "Rita Rep", representativeEmail: "rita@example.com" }),
+      );
+      expect(events.find((e) => e.type === "work_order.created")?.representative).toEqual({
+        name: "Rita Rep",
+        email: "rita@example.com",
+      });
+
+      events.length = 0;
+      await service.create(await studio(), fields({ representativeName: "Rita Rep" }));
+      expect(events.find((e) => e.type === "work_order.created")?.representative).toEqual({
+        name: "Dana Default",
+        email: "dana@example.com",
+      });
+    });
+
+    test("a countersignature records the signer's own email, not the default representative's", async () => {
+      await createWorkOrderIntegrations({ db }).saveRepresentative("studio", "studio-admin", {
+        name: "Dana Default",
+        email: "dana@example.com",
+      });
+      const wo = await active();
+      const [signature] = await db
+        .select()
+        .from(workOrderSignatures)
+        .where(
+          and(
+            eq(workOrderSignatures.workOrderId, wo.id),
+            eq(workOrderSignatures.role, "representative"),
+          ),
+        );
+      expect(signature?.email).toBe("studio-admin@example.com");
+    });
+
+    test("terminating tells the builder; a draft they never saw stays quiet", async () => {
+      const wo = await active();
+      events.length = 0;
+      await service.terminate(await studio(), { id: wo.id });
+      expect(events.map((e) => e.type)).toEqual(["work_order.terminated"]);
+      expect((await notificationsOf("carol")).map((n) => n.kind)).toContain(
+        "work_order_terminated",
+      );
+
+      const draft = await service.create(await studio(), fields());
+      events.length = 0;
+      await service.terminate(await studio(), { id: draft.id });
+      expect(events).toEqual([]);
+    });
+
+    test("deleting an offered work order tells the builder it was withdrawn", async () => {
+      const created = await service.create(await studio(), fields());
+      await service.offer(await studio(), { id: created.id });
+      events.length = 0;
+      await service.remove(await studio(), { id: created.id });
+      expect(events.map((e) => e.type)).toEqual(["work_order.withdrawn"]);
+      const [notice] = (await notificationsOf("carol")).filter(
+        (n) => n.kind === "work_order_withdrawn",
+      );
+      expect(notice?.link).toBe("/dashboard");
+
+      const draft = await service.create(await studio(), fields());
+      events.length = 0;
+      await service.remove(await studio(), { id: draft.id });
+      expect(events).toEqual([]);
     });
 
     test("accepting in the app proves the payout account", async () => {
@@ -994,7 +1072,7 @@ describe("work orders", () => {
       strongEvidence();
       const wo = await active({ tokenId: REAL_USDC });
       await service.collect(await studio(), { id: wo.id });
-      const draft = await service.mineDraftRequest(carol(), { id: wo.id });
+      const draft = await service.draftRequest(await studio(), { id: wo.id });
       expect(draft.contributionsMd).toContain("Carol shipped the search feature.");
       expect(draft.assessmentMd).toContain("Search unblocks onboarding.");
       const edited = await service.editRequest(carol(), {
@@ -1011,6 +1089,23 @@ describe("work orders", () => {
       expect(waiting?.request?.requested).toBe("500 USDC");
     });
   });
+  test("whether the period has started is judged in the agency's time zone", async () => {
+    service = createWorkOrdersService({ ...serviceDeps, timeZone: "Pacific/Kiritimati" });
+    await active();
+    const started = events.find((e) => e.type === "work_order.active");
+    expect(started?.workOrder.periodStarted).toBe(true);
+    expect(composeEmails(started!)[0]?.text).toContain("Your work period has started");
+  });
+
+  test("a builder drafting their own request isn't told it's ready", async () => {
+    const wo = await active();
+    const notes = (await notificationsOf("carol")).length;
+    const draft = await service.mineDraftRequest(carol(), { id: wo.id });
+    expect(draft.status).toBe("draft");
+    expect(events.map((e) => e.type)).not.toContain("request.report_ready");
+    expect((await notificationsOf("carol")).length).toBe(notes);
+  });
+
   describe("Google Docs and Drive", () => {
     const REAL_USDC = "17208628f84f5d6ad33f0da3bbbeb27ffcb398eac501a31bd6ad2011e36133a1";
 
@@ -1425,6 +1520,9 @@ describe("work orders", () => {
       expect((await notificationsOf("carol")).map((n) => n.kind)).not.toContain(
         "work_order_offered",
       );
+      const signFirst = events.find((e) => e.type === "work_order.sign_first");
+      expect(signFirst?.representative.email).toBe("rita@example.com");
+      expect(signFirst?.links.countersign).toBe("https://sign.example/envelope_1/representative");
 
       const admin = await service.get(await studio(), { id: created.id });
       expect(admin.status).toBe("offered");
@@ -1629,6 +1727,60 @@ describe("work orders", () => {
       expect(events.map((e) => e.type)).not.toContain("work_order.offered");
     });
 
+    test("asking for the payout account of a Documenso offer is refused: signing confirms it", async () => {
+      const created = await offered();
+      events.length = 0;
+      const notes = (await notificationsOf("carol")).length;
+      await refused(
+        service.requestPayeeConfirmation(await studio(), { id: created.id }),
+        "CONFIRMED_BY_SIGNING",
+      );
+      expect(events).toEqual([]);
+      expect((await notificationsOf("carol")).length).toBe(notes);
+    });
+
+    test("an envelope cancelled in Documenso puts the order back in draft and tells the agency", async () => {
+      const created = await offered();
+      events.length = 0;
+      documenso.last().status = "rejected";
+      const back = await service.get(await studio(), { id: created.id });
+      expect(back.status).toBe("draft");
+      expect(back.signing.esign?.error).toBe("Cancelled in Documenso");
+      expect(events.map((e) => e.type)).toEqual(["work_order.esign_cancelled"]);
+      expect(composeEmails(events[0]!).map((m) => m.to)).toEqual(["rita@example.com"]);
+      const kinds = (await notificationsOf("studio-admin")).map((n) => n.kind);
+      expect(kinds).toContain("work_order_esign_cancelled");
+      expect(kinds).not.toContain("work_order_declined");
+    });
+
+    test("a builder too early to sign is told the default representative signs first", async () => {
+      await createWorkOrderIntegrations({ db }).saveRepresentative("studio", "studio-admin", {
+        name: "Dana Default",
+        email: "dana@example.com",
+      });
+      const created = await service.create(await studio(), fields());
+      await service.offer(await studio(), { id: created.id });
+      const doc = await service.myDocument(carol(), { id: created.id });
+      await expect(
+        service.sign(carol(), { id: created.id, documentSha256: doc.sha256, name: "Carol" }),
+      ).rejects.toThrow("Dana Default signs it first");
+    });
+
+    test("terminating when Documenso can't withdraw a live envelope still tells the builder to ignore its link", async () => {
+      const created = await offered();
+      documenso.sign("representative", "2026-09-20T13:00:00.000Z");
+      documenso.cancel = async () => {
+        throw new Error("timeout");
+      };
+      events.length = 0;
+      const terminated = await service.terminate(await studio(), { id: created.id });
+      expect(terminated.signing.esign?.error).toContain("may still be able to sign there");
+      expect(events.map((e) => e.type)).toEqual(["work_order.withdrawn"]);
+      expect(composeEmails(events[0]!)[0]?.text).toContain(
+        "If you got a signing link for it, ignore it",
+      );
+    });
+
     async function completed() {
       const created = await offered();
       documenso.sign("representative", "2026-09-20T13:00:00.000Z");
@@ -1880,6 +2032,7 @@ describe("work orders", () => {
       expect(back.status).toBe("draft");
       expect(back.signing.esign?.error).toBe("Declined in Documenso: Wrong budget");
       expect(events.map((e) => e.type)).not.toContain("work_order.offered");
+      expect(events.map((e) => e.type)).not.toContain("work_order.declined");
 
       await service.offer(await studio(), { id: created.id });
       documenso.sign("representative", "2026-09-20T13:00:00.000Z");
@@ -1888,6 +2041,36 @@ describe("work orders", () => {
       const declined = await service.get(await studio(), { id: created.id });
       expect(declined.status).toBe("draft");
       expect(declined.signing.esign?.error).toBe("Declined in Documenso: Wrong budget");
+      const email = events.find((e) => e.type === "work_order.declined");
+      expect(email?.note).toBe("Wrong budget");
+    });
+
+    test("terminating an offer the builder never accepted tells them it was withdrawn, once the representative signed in Documenso", async () => {
+      const created = await offered();
+      documenso.sign("representative", "2026-09-20T13:00:00.000Z");
+      events.length = 0;
+      await service.terminate(await studio(), { id: created.id });
+      expect(events.map((e) => e.type)).toEqual(["work_order.withdrawn"]);
+      const kinds = (await notificationsOf("carol")).map((n) => n.kind);
+      expect(kinds).toContain("work_order_withdrawn");
+      expect(kinds).not.toContain("work_order_terminated");
+    });
+
+    test("terminating before the representative signed in Documenso doesn't tell the builder", async () => {
+      const created = await offered();
+      events.length = 0;
+      await service.terminate(await studio(), { id: created.id });
+      expect(events).toEqual([]);
+    });
+
+    test("withdrawing before the representative signed doesn't tell the builder", async () => {
+      const created = await offered();
+      events.length = 0;
+      await service.remove(await studio(), { id: created.id });
+      expect(events).toEqual([]);
+      expect((await notificationsOf("carol")).map((n) => n.kind)).not.toContain(
+        "work_order_withdrawn",
+      );
     });
 
     test("it isn't offered without both emails, or when Documenso refuses", async () => {