Out of Office Guide

Draft a client-ready instruction block for setting automatic replies properly — handling the two
traps: the internal/external split (most users don't know there are two messages) and the
forgot-to-set-dates auto-reply that runs forever. Prefer the web path (works for everyone, survives
version drift). Verify the environment before you write; when unsure, ask. Draft only — show me the reply as a draft to review first, and don't send it.

1. Verify the environment FIRST by checking the client's documentation and past tickets: which Outlook the user reaches most easily (prefer web as the primary
   path), and whether the client restricts external automatic replies (some do — if docs show
   external replies are blocked, the draft must say so instead of promising strangers get the
   message). If the mailbox in question is a shared mailbox, STOP — that's set admin-side; tell the
   tech and don't send user steps.
2. Write the web-first flow to end-user rules, one action per step with what-you'll-see cues:
   - Sign in to webmail; the settings gear; search or look for "Automatic replies" — cue: "a panel
     with an on/off switch at the top."
   - Turn it on, then tick the send-only-during-a-time-period option and set BOTH dates — with the
     why: "this makes it switch itself on and off; without dates you'll be that person whose 'back on
     Monday' reply is still going out in August." Suggest starting the evening before leave, ending
     the morning of return. (This set-both-dates instruction is the core of the skill — never draft
     an OOO guide without it and its plain-language why.)
   - The two message boxes, explained plainly: the first goes to coworkers, the second to everyone
     outside the company — "they can be the same text, but the outside one is what clients see, so
     keep it professional and light on detail."
   - What a good message contains (offer a fill-in skeleton with bracketed placeholders): dates back,
     who to contact meanwhile (name/address the user supplies — never invented; flag "NEEDS: covering
     contact" if unknown), and no more. Advise against oversharing travel details in the external
     message.
   - Optional calendar-tidy extras as a one-line "you may also see options to block your calendar —
     nice to have, optional."
   - Off-ramp: "If your settings don't show an Automatic replies option, stop and reply — your
     mailbox may be set up differently and we'll set it for you."
3. Include the verification step: "Send yourself a test from a personal address after it's on — you
   should get the external reply back within a minute or two" (only where external replies are
   permitted).
4. Assemble per the Email Baseline Standard.

Guardrails: the internal/external distinction appears in every draft; if the client blocks external
auto-replies, say so honestly rather than letting the user believe clients are being answered.
Never invent the covering colleague — the placeholder stays bracketed. Shared-mailbox OOO requests
never get user steps — route to the tech/admin side. The external-message security note (don't
advertise an empty house or exact travel plans) stays in. No admin steps (mailbox rules via admin
center, transport rules) in the user block. Localizable. The client's documentation is available only when those integrations are enabled.