[Fix] Session reminders fail when users request a delay in seconds

apps/docs/fast-sessions.mdx

@@ -163,13 +163,21 @@ list or cancel wakeups at any time; archiving a Session cancels all of its
 wakeups.
 
 Wakeups belong to the conversation and do not require an administrator. A
-Session may hold up to ten active wakeups, intervals range from one minute to
+Session may hold up to ten active wakeups, intervals range from one second to
 seven days, and recurring wakeups can be bounded by a run count or an end time.
 Intervals under five minutes must carry one of those bounds. A recurring wakeup
 whose turns fail five times in a row is retired. Deployment-wide recurring work
 that should run outside a conversation or report to a channel is an
 [automation](/automations) instead.
 
+Relative and interval schedules use `in <positive integer>s|m|h|d` and
+`every <positive integer>s|m|h|d`: seconds, minutes, hours, or days. Use `in 30s`,
+not fractional `in 0.5m`. For a short recurring check, use `every 30s x3` or an
+`until` end time; recurring intervals under five minutes still require a bound.
+Cron schedules remain five-field expressions, such as `cron 0 9 * * 1-5`.
+Delivery is best effort: `in 30s` does not guarantee a reply exactly 30 seconds
+later.
+
 ## Session and execution access
 
 Any signed-in deployment user with a Session link can view its timeline and

packages/cloud-agents/src/server/fast-agent/fast-agent-prompt.ts

@@ -350,7 +350,7 @@ ${reactionGuidance}
 - Use "cancel_task" only when the user explicitly asks to stop an active task.
 - Call a deployment MCP tool when it can answer the request. Fast receives the same actor-authorized remote and deployment-proxied MCP tool catalog as delegated tasks; local stdio servers remain sandbox-only. Servers listed with a tool prefix expose each tool individually with its native JSON schema. On-demand servers are reached through \`find_integration_tools\` (fetch the schema by server id and tool name, or search by keywords) followed by \`call_integration_tool\`; the same acknowledgement, duplicate, and audit rules apply to both paths.
 - Use \`roomote_manage_custom_automations\` for custom automation lifecycle requests. It uses the current user's deployment authorization, is admin-only, and is unavailable to advisor and judge subagents. List before modifying an existing automation, use "list_models" before setting a model override, use update with "enabled" to enable or disable, and use "run_now" rather than "launch_task" to test an automation. Communicate first on a human-authored turn; platform events remain exempt. Delete only when the user explicitly requests it, and after creating an automation ask whether they want to run it now.
-- Use "manage_wakeups" when the user wants a reminder, a delayed follow-up, or a recurring check that reports back into this conversation ("remind me in 20 minutes", "check every 10 minutes until CI is green", "every weekday at 9 ping me with open PRs"). The schedule is one short string: "in 20m" for a reminder, "every 10m" or "every 1m x3" for a repeating check, "cron 0 9 * * 1-5" for a calendar schedule. Send only the fields the action needs. It is scoped to this conversation and available to every participant. Do not use \`roomote_manage_custom_automations\` for conversation-scoped reminders, and never sleep or poll inside a turn instead of scheduling a wakeup. After creating one, confirm the plan and the next run time in one sentence; when the user says stop or cancel, use action "cancel".
+- Use "manage_wakeups" when the user wants a reminder, a delayed follow-up, or a recurring check that reports back into this conversation ("remind me in 20 minutes", "check every 10 minutes until CI is green", "every weekday at 9 ping me with open PRs"). The schedule is one short string: "in <positive integer>s|m|h|d" for a reminder, "every <positive integer>s|m|h|d" for a repeating check, "cron 0 9 * * 1-5" for a five-field calendar schedule. Prefer "in 30s", not fractional "in 0.5m". Recurring intervals under five minutes require an x<count> or until bound, such as "every 30s x3". Delivery is best effort; never promise an exact 30-second reply. Send only the fields the action needs. It is scoped to this conversation and available to every participant. Do not use \`roomote_manage_custom_automations\` for conversation-scoped reminders, and never sleep or poll inside a turn instead of scheduling a wakeup. After creating one, confirm the plan and the next run time in one sentence; when the user says stop or cancel, use action "cancel".
 
 ${recurringAutomationGuidance}
 - You may make multiple deployment MCP calls when needed, one at a time. Stop as soon as you have enough evidence and never repeat an identical call.

packages/cloud-agents/src/server/session-wakeups/parse.ts

@@ -17,31 +17,36 @@ export type ParsedSessionWakeupSchedule = {
   until: Date | null;
 };
 
-const UNIT_MINUTES: Record<string, number> = {
-  m: 1,
-  min: 1,
-  mins: 1,
-  minute: 1,
-  minutes: 1,
-  h: 60,
-  hr: 60,
-  hrs: 60,
-  hour: 60,
-  hours: 60,
-  d: 24 * 60,
-  day: 24 * 60,
-  days: 24 * 60,
+const UNIT_SECONDS: Record<string, number> = {
+  s: 1,
+  sec: 1,
+  secs: 1,
+  second: 1,
+  seconds: 1,
+  m: 60,
+  min: 60,
+  mins: 60,
+  minute: 60,
+  minutes: 60,
+  h: 3600,
+  hr: 3600,
+  hrs: 3600,
+  hour: 3600,
+  hours: 3600,
+  d: 24 * 3600,
+  day: 24 * 3600,
+  days: 24 * 3600,
 };
 
 // Every pattern below runs on text whose whitespace has already been
 // collapsed to single spaces and whose length is capped by the contract, so
 // the patterns use literal single spaces and stay linear.
-const DURATION = String.raw`(\d+) ?(m|min|mins|minute|minutes|h|hr|hrs|hour|hours|d|day|days)`;
+const DURATION = String.raw`(\d+) ?(s|sec|secs|second|seconds|m|min|mins|minute|minutes|h|hr|hrs|hour|hours|d|day|days)`;
 const DURATION_RE = new RegExp(`^${DURATION}$`, 'i');
 const IN_RE = new RegExp(`^(?:once )?in ${DURATION}$`, 'i');
 const AT_RE = /^(?:once )?at (\S+)$/i;
 const EVERY_RE = new RegExp(
-  `^every (?:${DURATION}|(minute|hour|day))(?: (.*))?$`,
+  `^every (?:${DURATION}|(second|minute|hour|day))(?: (.*))?$`,
   'i',
 );
 const CRON_RE = /^cron ((?:\S+ ){4}\S+)(?: (.*))?$/i;
@@ -59,7 +64,7 @@ function invalid(text: string, detail?: string): SessionWakeupValidationError {
 
 function durationMinutes(amount: string, unit: string): number {
   const minutes =
-    Number.parseInt(amount, 10) * UNIT_MINUTES[unit.toLowerCase()]!;
+    (Number.parseInt(amount, 10) * UNIT_SECONDS[unit.toLowerCase()]!) / 60;
   if (!Number.isFinite(minutes) || minutes <= 0) {
     throw new SessionWakeupValidationError('A duration must be positive.');
   }
@@ -147,7 +152,7 @@ export function parseSessionWakeupSchedule(
   const everyMatch = EVERY_RE.exec(text);
   if (everyMatch) {
     const everyMinutes = everyMatch[3]
-      ? UNIT_MINUTES[everyMatch[3].toLowerCase()]!
+      ? UNIT_SECONDS[everyMatch[3].toLowerCase()]! / 60
       : durationMinutes(everyMatch[1]!, everyMatch[2]!);
     const normalized = normalizeSessionWakeupSchedule(
       { mode: 'interval', everyMinutes },

packages/cloud-agents/src/server/session-wakeups/schedule.ts

@@ -1,10 +1,9 @@
 import { CronExpressionParser } from 'cron-parser';
 
 import {
-  SESSION_WAKEUP_MAX_INTERVAL_MINUTES,
   SESSION_WAKEUP_MAX_ONCE_HORIZON_MINUTES,
-  SESSION_WAKEUP_MIN_INTERVAL_MINUTES,
   SESSION_WAKEUP_UNCAPPED_MIN_INTERVAL_MINUTES,
+  sessionWakeupScheduleSchema,
   type SessionWakeupSchedule,
 } from '@roomote/types';
 
@@ -88,8 +87,20 @@ export function normalizeSessionWakeupSchedule(
           'A once schedule needs inMinutes or at.',
         );
       }
+      if (
+        hasDelay &&
+        !sessionWakeupScheduleSchema.safeParse({
+          mode: 'once',
+          at: now.toISOString(),
+          inMinutes: input.inMinutes,
+        }).success
+      ) {
+        throw new SessionWakeupValidationError(
+          'A once delay must be a positive whole number of seconds, at most 30 days out.',
+        );
+      }
       const at = hasDelay
-        ? new Date(now.getTime() + input.inMinutes! * MINUTE_MS)
+        ? new Date(now.getTime() + Math.round(input.inMinutes! * MINUTE_MS))
         : parseIsoDate(input.at!, 'at');
       if (at.getTime() <= now.getTime()) {
         throw new SessionWakeupValidationError(
@@ -114,18 +125,16 @@ export function normalizeSessionWakeupSchedule(
       };
     }
     case 'interval': {
-      if (
-        !Number.isInteger(input.everyMinutes) ||
-        input.everyMinutes < SESSION_WAKEUP_MIN_INTERVAL_MINUTES ||
-        input.everyMinutes > SESSION_WAKEUP_MAX_INTERVAL_MINUTES
-      ) {
+      if (!sessionWakeupScheduleSchema.safeParse(input).success) {
         throw new SessionWakeupValidationError(
-          `everyMinutes must be a whole number between ${SESSION_WAKEUP_MIN_INTERVAL_MINUTES} and ${SESSION_WAKEUP_MAX_INTERVAL_MINUTES}.`,
+          'An interval must be a positive whole number of seconds, at most 7 days.',
         );
       }
       return {
         schedule: { mode: 'interval', everyMinutes: input.everyMinutes },
-        firstRunAt: new Date(now.getTime() + input.everyMinutes * MINUTE_MS),
+        firstRunAt: new Date(
+          now.getTime() + Math.round(input.everyMinutes * MINUTE_MS),
+        ),
       };
     }
     case 'cron': {
@@ -168,7 +177,9 @@ export function computeNextSessionWakeupRunAt(
       return at.getTime() > from.getTime() ? at : null;
     }
     case 'interval':
-      return new Date(from.getTime() + schedule.everyMinutes * MINUTE_MS);
+      return new Date(
+        from.getTime() + Math.round(schedule.everyMinutes * MINUTE_MS),
+      );
     case 'cron':
       return nextCronOccurrence(schedule.expression, schedule.timezone, from);
   }
@@ -274,6 +285,10 @@ function estimateCronMinGapMinutes(
 }
 
 function formatMinutes(minutes: number): string {
+  if (!Number.isInteger(minutes)) {
+    const seconds = Math.round(minutes * 60);
+    return `${seconds} second${seconds === 1 ? '' : 's'}`;
+  }
   if (minutes % (24 * 60) === 0) {
     const days = minutes / (24 * 60);
     return `${days} day${days === 1 ? '' : 's'}`;