diff --git a/apps/web/src/pages/workspace/index.tsx b/apps/web/src/pages/workspace/index.tsx
index 3fd7faa5..2604adb1 100644
--- a/apps/web/src/pages/workspace/index.tsx
+++ b/apps/web/src/pages/workspace/index.tsx
@@ -71,7 +71,11 @@ import { cardDocuments } from "./collaboration.ts";
 import { useFiledVersions } from "./filed-versions.tsx";
 import { threadUpdates } from "./specialist-updates.tsx";
 import { useSettledApprovals, type OpenApproval } from "./settled-approvals.ts";
-import { useTypedYes } from "./typed-yes.tsx";
+import {
+  chooseApproachWithOpenApproval,
+  deliverWithOpenApproval,
+  useTypedYes,
+} from "./typed-yes.tsx";
 import { asksAbout, chosenApproach } from "./approach-choice.ts";
 import { selectedDeliverable } from "./reading-selection.ts";
 import {
@@ -849,6 +853,9 @@ export function StageWorkspace({
       setApprovalBusy(false);
     }
   };
+  const openApproval = pendingApprovals.find(
+    (approval) => approval.packages === undefined,
+  );
   // Choosing an approach is the person's yes to the version's open ask; the message names the pick.
   const chooseApproach = async (
     message: string,
@@ -863,32 +870,34 @@ export function StageWorkspace({
               approval.packages === undefined &&
               asksAbout(approval, kind, version),
           );
-    if (asked !== undefined) {
-      const fault = await onDecideApproval({
-        approvalId: asked.approvalId,
-        choice: "yes",
-      });
-      if (fault !== null) return fault;
-    }
-    return (await deliver(message)) ? null : wording.approaches.notSent;
+    return chooseApproachWithOpenApproval({
+      askedApprovalId: asked?.approvalId,
+      openApprovalId: openApproval?.approvalId,
+      decide: onDecideApproval,
+      deliver: () => deliver(message),
+      notSent: wording.approaches.notSent,
+    });
   };
-  const openApproval = pendingApprovals.find(
-    (approval) => approval.packages === undefined,
-  );
+  const sendWithApproval = (body: string, clearComposer = false) =>
+    deliverWithOpenApproval({
+      openApprovalId: openApproval?.approvalId,
+      decide: onDecideApproval,
+      deliver: () => deliver(body, clearComposer),
+    });
   const sendNow = () => {
     setCaution(null);
-    void deliver(value, true);
+    void sendWithApproval(value, true);
   };
   const restoreToComposer = (message: string) =>
     setValue((current) => (current.trim().length === 0 ? message : current));
+  const undoTypedYes = async (message: string) => {
+    if (!(await sendWithApproval(message))) restoreToComposer(message);
+  };
   const typedYes = useTypedYes({
     pending: pendingApprovals.map((approval) => approval.approvalId),
     onApprove: (approvalId) =>
       void onDecideApproval({ approvalId, choice: "yes" }),
-    onUndo: (message) =>
-      void deliver(message).then((sent) => {
-        if (!sent) restoreToComposer(message);
-      }),
+    onUndo: (message) => void undoTypedYes(message),
     onDropped: restoreToComposer,
   });
   const shell = useShellReply(documentPaneRef);
@@ -1232,7 +1241,7 @@ export function StageWorkspace({
                         },
                       })}
                   {...(sentId === undefined ? {} : { sentId })}
-                  onAnswerQuestions={(reply) => deliver(reply)}
+                  onAnswerQuestions={(reply) => sendWithApproval(reply)}
                   questionsDisabled={sending || archived}
                 >
                   {archived ? (
@@ -1365,7 +1374,7 @@ export function StageWorkspace({
                           type="button"
                           variant="outline"
                           size="sm"
-                          onClick={() => void deliver(reply)}
+                          onClick={() => void sendWithApproval(reply)}
                         >
                           {reply}
                         </UiButton>
diff --git a/apps/web/src/pages/workspace/typed-yes.test.ts b/apps/web/src/pages/workspace/typed-yes.test.ts
index 0fc5b661..5e288226 100644
--- a/apps/web/src/pages/workspace/typed-yes.test.ts
+++ b/apps/web/src/pages/workspace/typed-yes.test.ts
@@ -1,5 +1,9 @@
 import { expect, test } from "bun:test";
-import { isAffirmation } from "./typed-yes.tsx";
+import {
+  chooseApproachWithOpenApproval,
+  deliverWithOpenApproval,
+  isAffirmation,
+} from "./typed-yes.tsx";
 
 test("only a whole plain affirmation approves", () => {
   for (const message of [
@@ -22,3 +26,90 @@ test("only a whole plain affirmation approves", () => {
   ])
     expect(isAffirmation(message)).toBe(false);
 });
+
+test("sending a message while a coordinator approval is open denies it first", async () => {
+  const steps: string[] = [];
+  const sent = await deliverWithOpenApproval({
+    openApprovalId: "appr-design",
+    decide: async (decision) => {
+      steps.push(`decide:${decision.approvalId}:${decision.choice}`);
+      return null;
+    },
+    deliver: async () => {
+      steps.push("deliver");
+      return true;
+    },
+  });
+  expect(sent).toBe(true);
+  expect(steps).toEqual(["decide:appr-design:no", "deliver"]);
+});
+
+test("sending a message when no coordinator approval is open delivers directly", async () => {
+  const steps: string[] = [];
+  const sent = await deliverWithOpenApproval({
+    openApprovalId: undefined,
+    decide: async () => {
+      steps.push("decide");
+      return null;
+    },
+    deliver: async () => {
+      steps.push("deliver");
+      return true;
+    },
+  });
+  expect(sent).toBe(true);
+  expect(steps).toEqual(["deliver"]);
+});
+
+test("a failed denial stops before delivering the message", async () => {
+  const steps: string[] = [];
+  const sent = await deliverWithOpenApproval({
+    openApprovalId: "appr-design",
+    decide: async () => {
+      steps.push("decide");
+      return "That decision was not saved.";
+    },
+    deliver: async () => {
+      steps.push("deliver");
+      return true;
+    },
+  });
+  expect(sent).toBe(false);
+  expect(steps).toEqual(["decide"]);
+});
+
+test("choosing an approach approves a matching ask without denying it and denies an unrelated open ask", async () => {
+  const matchingSteps: string[] = [];
+  const matchingFault = await chooseApproachWithOpenApproval({
+    askedApprovalId: "appr-approaches",
+    openApprovalId: "appr-approaches",
+    decide: async (decision) => {
+      matchingSteps.push(`decide:${decision.approvalId}:${decision.choice}`);
+      return null;
+    },
+    deliver: async () => {
+      matchingSteps.push("deliver");
+      return true;
+    },
+    notSent: "not sent",
+  });
+  expect(matchingFault).toBeNull();
+  expect(matchingSteps).toEqual(["decide:appr-approaches:yes", "deliver"]);
+
+  const unrelatedSteps: string[] = [];
+  const unrelatedFault = await chooseApproachWithOpenApproval({
+    askedApprovalId: undefined,
+    openApprovalId: "appr-design",
+    decide: async (decision) => {
+      unrelatedSteps.push(`decide:${decision.approvalId}:${decision.choice}`);
+      return null;
+    },
+    deliver: async () => {
+      unrelatedSteps.push("deliver");
+      return true;
+    },
+    notSent: "not sent",
+  });
+  expect(unrelatedFault).toBeNull();
+  expect(unrelatedSteps).toEqual(["decide:appr-design:no", "deliver"]);
+});
diff --git a/apps/web/src/pages/workspace/typed-yes.tsx b/apps/web/src/pages/workspace/typed-yes.tsx
index a60e4dad..3ed7054a 100644
--- a/apps/web/src/pages/workspace/typed-yes.tsx
+++ b/apps/web/src/pages/workspace/typed-yes.tsx
@@ -98,6 +98,59 @@ export function useTypedYes({
   return { held, hold, undo };
 }
 
+/**
+ * Sends a message while a coordinator approval card may be open: denies the open card first
+ * so the parked coordinator wakes to read the message.
+ */
+export async function deliverWithOpenApproval({
+  openApprovalId,
+  decide,
+  deliver,
+}: {
+  openApprovalId: string | undefined;
+  decide: (decision: {
+    approvalId: string;
+    choice: "yes" | "always" | "no";
+  }) => Promise<string | null>;
+  deliver: () => Promise<boolean>;
+}): Promise<boolean> {
+  if (openApprovalId !== undefined) {
+    const fault = await decide({ approvalId: openApprovalId, choice: "no" });
+    if (fault !== null) return false;
+  }
+  return deliver();
+}
+
+/**
+ * Picks an approach while a coordinator approval card may be open: approves when the open
+ * card asks about the chosen version, or denies any other open coordinator card first.
+ */
+export async function chooseApproachWithOpenApproval({
+  askedApprovalId,
+  openApprovalId,
+  decide,
+  deliver,
+  notSent,
+}: {
+  askedApprovalId: string | undefined;
+  openApprovalId: string | undefined;
+  decide: (decision: {
+    approvalId: string;
+    choice: "yes" | "always" | "no";
+  }) => Promise<string | null>;
+  deliver: () => Promise<boolean>;
+  notSent: string;
+}): Promise<string | null> {
+  if (askedApprovalId !== undefined) {
+    const fault = await decide({ approvalId: askedApprovalId, choice: "yes" });
+    if (fault !== null) return fault;
+  } else if (openApprovalId !== undefined) {
+    const fault = await decide({ approvalId: openApprovalId, choice: "no" });
+    if (fault !== null) return fault;
+  }
+  return (await deliver()) ? null : notSent;
+}
+
 /** The countdown on the card it will approve, with its undo. */
 export function TypedYesCountdown({
   held,