improvement(email): reply-to help@sim.ai for lifecycle and billing emails

[waleedlatif1]

Summary

• Onboarding follow-up (5-day), payment-failed, and abandoned-checkout emails now reply-to the shared help inbox (help@sim.ai) instead of a personal email address
• Added getHelpEmailAddress() in lib/messaging/email/utils.ts and reused it in the help route, removing a duplicated inline expression

Type of Change

• Improvement

Testing

• bun run type-check clean on changed files
• vitest run lib/billing/webhooks/invoices.test.ts passing
• bunx biome check clean on changed files

Checklist

• Code follows project style guidelines
• Self-reviewed my changes
• Tests added/updated and passing
• No new warnings introduced
• I confirm that I have read and agree to the terms outlined in the Contributor License Agreement (CLA)

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1 Skipped Deployment

Project	Deployment	Actions	Updated (UTC)
docs	Skipped		Jul 7, 2026 6:57pm

[cursor]

PR Summary

Low Risk
Narrow email header routing change with no auth or payment logic changes; behavior is covered by an updated invoice webhook test.

Overview
Introduces getHelpEmailAddress() in lib/messaging/email/utils.ts as the single source for the shared help inbox (help@ + email domain), and routes lifecycle, billing, and help-form mail through it for reply-to (and help submissions for to / confirmation reply-to).

Lifecycle and billing notification emails (onboarding follow-up, abandoned checkout, payment failed) still use getPersonalEmailFrom() for the from address but now set reply-to to the help inbox instead of the personal address embedded in PERSONAL_EMAIL_FROM. The help API drops duplicated inline help@… construction in favor of the same helper.

Docs on getPersonalEmailFrom() clarify that lifecycle/billing should not use its replyTo field. A new invoice webhook test asserts payment-failure emails send with replyTo: help@….

^{Reviewed by Cursor Bugbot for commit de04785. Configure here.}

[greptile-apps]

Greptile Summary

This PR routes replies on lifecycle (onboarding follow-up), billing (payment-failed, abandoned-checkout), and help confirmation emails to the shared help@sim.ai inbox instead of a personal address. It also extracts the previously duplicated help@… address expression into a single getHelpEmailAddress() utility.

• lib/messaging/email/utils.ts: New getHelpEmailAddress() replaces two inline help@${env.EMAIL_DOMAIN || getEmailDomain()} constructions, giving one place to change the address in the future.
• Three call sites (lifecycle-email.ts, checkout.ts, invoices.ts): destructure only from from getPersonalEmailFrom() and set replyTo from getHelpEmailAddress(), ensuring replies from recipients go to the team inbox.
• invoices.test.ts: Adds a dedicated test asserting sendEmail receives replyTo: 'help@sim.test', locking in the wiring introduced by this PR.

Confidence Score: 5/5

Safe to merge — the change is additive, isolated to email reply-to wiring, and backed by a new test that verifies the correct address reaches sendEmail.

All three call sites perform a mechanical swap of one well-understood expression for a named utility with identical semantics; no branching logic or auth paths are touched. The new invoices.test.ts case confirms the end-to-end wiring, and the existing test suite remains green.

No files require special attention.

Important Files Changed

Filename	Overview
apps/sim/lib/messaging/email/utils.ts	Adds getHelpEmailAddress() using the same `help@${env.EMAIL_DOMAIN
apps/sim/app/api/help/route.ts	Replaces two inline `help@${env.EMAIL_DOMAIN
apps/sim/background/lifecycle-email.ts	Switches the onboarding follow-up email reply-to from getPersonalEmailFrom().replyTo (which could be undefined or a personal address) to getHelpEmailAddress().
apps/sim/lib/billing/webhooks/checkout.ts	Same reply-to switch as lifecycle-email.ts, applied to the abandoned-checkout email path.
apps/sim/lib/billing/webhooks/invoices.ts	Same reply-to switch as lifecycle-email.ts, applied to the payment-failure email path.
apps/sim/lib/billing/webhooks/invoices.test.ts	Adds getHelpEmailAddress mock and a new test case asserting sendEmail is called with replyTo: 'help@sim.test' for payment-failure emails, locking in the new behaviour.

Sequence Diagram

%%{init: {'theme': 'neutral'}}%%
sequenceDiagram
    participant Trigger as Trigger (lifecycle / Stripe webhook)
    participant Handler as Email Handler
    participant Utils as email/utils.ts
    participant Mailer as sendEmail()
    participant Recipient as User Inbox

    Trigger->>Handler: event fires
    Handler->>Utils: getPersonalEmailFrom() returns from
    Handler->>Utils: "getHelpEmailAddress() returns help@sim.ai"
    Handler->>Mailer: "sendEmail with from and replyTo help@sim.ai"
    Mailer->>Recipient: delivers email
    Recipient-->>Handler: "user replies routed to help@sim.ai"

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%%{init: {'theme': 'base', 'themeVariables': {"darkMode": true, "background": "#0d1117", "primaryColor": "#21262d", "primaryTextColor": "#e6edf3", "primaryBorderColor": "#8b949e", "lineColor": "#8b949e", "textColor": "#e6edf3", "edgeLabelBackground": "#161b22", "actorBkg": "#21262d", "actorBorder": "#8b949e", "actorTextColor": "#e6edf3", "actorLineColor": "#8b949e", "signalColor": "#8b949e", "signalTextColor": "#e6edf3", "noteBkgColor": "#373320", "noteBorderColor": "#d4a72c", "noteTextColor": "#f0e6c0", "labelBoxBkgColor": "#21262d", "labelBoxBorderColor": "#8b949e", "labelTextColor": "#e6edf3", "loopTextColor": "#e6edf3", "activationBkgColor": "#30363d", "activationBorderColor": "#8b949e"}}}%%
sequenceDiagram
    participant Trigger as Trigger (lifecycle / Stripe webhook)
    participant Handler as Email Handler
    participant Utils as email/utils.ts
    participant Mailer as sendEmail()
    participant Recipient as User Inbox

    Trigger->>Handler: event fires
    Handler->>Utils: getPersonalEmailFrom() returns from
    Handler->>Utils: "getHelpEmailAddress() returns help@sim.ai"
    Handler->>Mailer: "sendEmail with from and replyTo help@sim.ai"
    Mailer->>Recipient: delivers email
    Recipient-->>Handler: "user replies routed to help@sim.ai"

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[waleedlatif1]

@greptile

[waleedlatif1]

@cursor review

[cursor]

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^{Reviewed by Cursor Bugbot for commit de04785. Configure here.}