diff --git a/packages/protocol/src/schedule/cron-expression.ts b/packages/protocol/src/schedule/cron-expression.ts
index cc93652afa..5cfffbbb1b 100644
--- a/packages/protocol/src/schedule/cron-expression.ts
+++ b/packages/protocol/src/schedule/cron-expression.ts
@@ -5,6 +5,7 @@ interface CronFieldBounds {
 }
 
 export interface CronFieldMatcher {
+  isWildcard: boolean;
   matches(value: number): boolean;
 }
 
@@ -101,6 +102,7 @@ function parseField(source: string, bounds: CronFieldBounds): CronFieldMatcher {
   }
 
   return {
+    isWildcard: trimmed.startsWith("*"),
     matches(value: number): boolean {
       return allowed.has(value);
     },
diff --git a/packages/server/src/server/schedule/cron.test.ts b/packages/server/src/server/schedule/cron.test.ts
index 9d4172ff27..da8d9760ed 100644
--- a/packages/server/src/server/schedule/cron.test.ts
+++ b/packages/server/src/server/schedule/cron.test.ts
@@ -20,6 +20,37 @@ describe("schedule cron cadence", () => {
     expect(next.toISOString()).toBe("2026-01-05T09:15:00.000Z");
   });
 
+  test("matches either restricted day field", () => {
+    const next = computeNextRunAt(
+      { type: "cron", expression: "0 9 1 * 1" },
+      new Date("2026-10-17T00:00:00.000Z"),
+    );
+
+    expect(next.toISOString()).toBe("2026-10-19T09:00:00.000Z");
+  });
+
+  test.each([
+    ["0 9 1 * 1", "2026-10-30T10:00:00.000Z", "2026-11-01T09:00:00.000Z"],
+    ["0 9 1 * *", "2026-10-17T00:00:00.000Z", "2026-11-01T09:00:00.000Z"],
+    ["0 9 * * 1", "2026-10-17T00:00:00.000Z", "2026-10-19T09:00:00.000Z"],
+    ["0 9 */2 * 1", "2026-10-19T09:00:00.000Z", "2026-11-09T09:00:00.000Z"],
+    ["0 9 1-31 * 1", "2026-10-17T00:00:00.000Z", "2026-10-17T09:00:00.000Z"],
+    ["0 9 1,15 * 5", "2026-10-17T00:00:00.000Z", "2026-10-23T09:00:00.000Z"],
+  ])("honors day-field semantics for %s", (expression, after, expected) => {
+    const next = computeNextRunAt({ type: "cron", expression }, new Date(after));
+
+    expect(next.toISOString()).toBe(expected);
+  });
+
+  test("matches either restricted day field in the schedule's time zone", () => {
+    const next = computeNextRunAt(
+      { type: "cron", expression: "0 9 1 * 1", timezone: "America/New_York" },
+      new Date("2026-10-17T00:00:00.000Z"),
+    );
+
+    expect(next.toISOString()).toBe("2026-10-19T13:00:00.000Z");
+  });
+
   test("computes timezone cron matches at the requested wall-clock time", () => {
     const winter = computeNextRunAt(
       { type: "cron", expression: "0 9 * * 1-5", timezone: "America/New_York" },
diff --git a/packages/server/src/server/schedule/cron.ts b/packages/server/src/server/schedule/cron.ts
index 21491ff065..972289322d 100644
--- a/packages/server/src/server/schedule/cron.ts
+++ b/packages/server/src/server/schedule/cron.ts
@@ -99,19 +99,24 @@ export function computeNextRunAt(cadence: ScheduleCadence, after: Date): Date {
   }
 
   const cron = parseCronExpression(cadence.expression);
+  const hasWildcardDay = cron.dayOfMonth.isWildcard || cron.dayOfWeek.isWildcard;
   const readDateParts = createCronDatePartsReader(cadence.timezone);
   const limit = 366 * 24 * 60;
   let cursor = startOfNextMinute(after);
 
   for (let index = 0; index < limit; index += 1) {
     const { minute, hour, dayOfMonth, month, dayOfWeek } = readDateParts(cursor);
+    const dayOfMonthMatches = cron.dayOfMonth.matches(dayOfMonth);
+    const dayOfWeekMatches = cron.dayOfWeek.matches(dayOfWeek);
+    const bothDaysMatch = dayOfMonthMatches && dayOfWeekMatches;
+    const eitherDayMatches = dayOfMonthMatches || dayOfWeekMatches;
+    const dayMatches = hasWildcardDay ? bothDaysMatch : eitherDayMatches;
 
     if (
       cron.minute.matches(minute) &&
       cron.hour.matches(hour) &&
-      cron.dayOfMonth.matches(dayOfMonth) &&
       cron.month.matches(month) &&
-      cron.dayOfWeek.matches(dayOfWeek)
+      dayMatches
     ) {
       return cursor;
     }