# Shortwave alternative for Outlook, Microsoft 365 and iCloud

> Shortwave needs a Gmail account and does not support Microsoft 365. Alternatives for Outlook, Exchange, iCloud and custom domains, and what an agent may do.

Updated: 2026-10-23 · Fact-checked: 2026-10-23 · Canonical: https://commandmail.app/en/alternatives/shortwave · Deutsch: https://commandmail.app/de/alternativen/shortwave-alternative.md

Shortwave only works with Gmail and Google Workspace: you sign in with a Google account, Microsoft 365 and Exchange are not supported at this time, and Outlook.com addresses can be forwarded in but not used to send.[^1] For Gmail and Microsoft accounts there is Superhuman; for Outlook, iCloud, Exchange and other IMAP accounts there is, for example, Canary.[^10][^13] Command Mail fits when your own AI agent should read, sort and draft for all of those addresses in one place.

Command Mail is our product. We read the Shortwave pages, Spark, Canary and Command Mail on 2026-10-23 and the Superhuman help center on 2026-10-21. Each source lists its own retrieval date.[^1][^9][^11][^12][^14]

## Where Shortwave is strong

Shortwave puts a conversational assistant inside the inbox. Ask it to "organize my inbox" and it proposes grouped actions such as archiving low-priority threads, labelling, deleting junk and creating todos, and you confirm each step.[^7] It drafts replies in your voice by learning from your sent mail, answers questions with AI search, and can send calendar invites.[^7][^3]

The Business plans cost $30, $45 (Premier) and $120 (Max) per seat per month. Depending on the tier you get 3, 10 or 50 AI filters that act on new mail from a plain-language prompt, and AI search across five years or your full history.[^3] One paid seat covers every account of your own that is signed in on the same device.[^4]

On security, Shortwave lists a CASA Tier 2 assessment with an annual audit and Google's verification for sensitive Gmail scopes. Data is stored in Google Cloud; the other sub-processors are OpenAI, Anthropic and Pinecone, and your mail is not used to train third-party models.[^6] For SOC 2 Type II or GDPR requirements, Shortwave refers you to its support team.[^6]

## Why people look for an alternative

One reason to look elsewhere is account support. Shortwave's own help says it only works with Gmail and Google Workspace.[^1] Other providers go through a bridge: forward their mail to a Gmail account, then add the address under Gmail's "Send mail as" with the provider's SMTP server and an app password. Shortwave describes Yahoo, iCloud, Fastmail and Zoho as fully supported this way.[^1]

Microsoft is where the bridge breaks. Outlook.com, Hotmail and Live are receive-only: mail arrives by forwarding, but replies leave from the Gmail address, because Microsoft requires OAuth2 and "Send mail as" does not support it.[^2] Microsoft 365 and Exchange are not supported at all, and there is no timeline.[^1]

The second reason is the agent. Shortwave's assistant can call other tools over MCP, for example Notion, Asana or HubSpot.[^5] That connection points outward from Shortwave. If you want Claude, ChatGPT or an agent you built yourself to work in your mailbox, we found no documented way in; neither the help pages nor the pricing page mention an MCP server for outside agents.

The third reason is the plan. According to the pricing table, Free and the individual Pro plan include neither AI filters nor AI integrations, and Free searches only the last 90 days and adds a "Sent with Shortwave" signature.[^3] The page renders the individual plan prices with a script, and we did not extract them.

## Options at a glance

| Product | Accounts | Price (see source date) | Access for outside agents |
|---|---|---|---|
| Shortwave | Gmail, Google Workspace; others via forwarding to Gmail, no Microsoft 365[^1] | Business $30, Premier $45, Max $120 per seat per month[^3] | MCP only as a client of its own assistant, Business and up, beta[^5] |
| Superhuman | Gmail, Outlook[^10] | Starter $30/month, Business $40/month[^9] | Mail MCP server on Business, read-only mode available[^10] |
| Spark | unlimited email accounts, also on Free[^11] | Free €0, Plus €10, Pro €22 per month[^11] | Spark CLI with read access, triage on Pro; no MCP server found[^11] |
| Canary Mail | Gmail, Outlook, iCloud, Exchange, IMAP[^13] | Free $0, Growth $36/year, Pro+ $100/year[^12] | none found |
| Command Mail | any address via forwarding[^14] | Free €0, Pro €19 or €29 per month[^14] | hosted MCP server, CLI, permissions per connection, autonomy per mailbox[^14] |

"Not found" means the vendor's pages said nothing about it on the retrieval date. That may change.

## Superhuman: a client for Gmail and Outlook

If Outlook is why you are leaving Shortwave, Superhuman is an option for Gmail and Outlook accounts. Starter is $30 a month or $300 a year, Business $40 a month.[^9][^10]

Superhuman also runs its own MCP server. Claude, ChatGPT, Codex, Cursor and other clients can search, draft and send through it, and several Gmail and Outlook accounts can be connected in one session. It requires Business, and a read-only mode exists.[^10] According to Superhuman's help center, accounts must be hosted by Google or Microsoft 365; on-premises Exchange servers are not supported.[^10]

## Spark and Canary: many account types at a low price

Readdle's Spark takes unlimited email accounts even on the free plan. Plus is €10 a month and Pro €22, with the Spark +AI assistant and meeting notes.[^11] For agents, the pricing page lists a Spark CLI with read access, upgraded to triage access on Pro. We found no MCP server.[^11]

Canary Mail supports Gmail, Outlook, iCloud, Exchange and IMAP, which makes it one of the few options here that names Exchange explicitly.[^13] Growth is $36 a year and Pro+ $100 a year, next to a free plan.[^12] Canary says triage runs on the device, while drafts and summaries use cloud AI.[^13] It does not mention any access for your own agents.

If what you want is a mail client that talks to Outlook, iCloud, Exchange and IMAP accounts directly, Canary documents exactly that. Spark's pricing page does not list which providers it supports, so check your account before you pay.[^11][^13]

## Command Mail: an inbox your own agent works in

Command Mail is one inbox for all of your addresses, built so your AI agent can work in it.[^14] You forward each address to a private intake address, whether it sits at Gmail, Outlook.com, iCloud or on your own domain, so no Gmail account is needed in between. You then connect Claude, ChatGPT, Codex, Cursor or another agent through the hosted MCP server at `https://commandmail.app/mcp` or through the CLI.[^14][^16]

When you connect an agent you pick its permissions: read, save drafts, send exactly one approved draft revision, or send on its own. Sending without approval starts switched off. Each mailbox also has an autonomy level, and on `suggest` and `rules` logged organizing actions such as archiving or deleting become suggestions and only approved drafts go out. Read markers, stars and labels take effect immediately there, and on `rules` enabled rules can act directly.[^14][^18] Reading is account-wide, though: permissions apply to every mailbox in the account, and the autonomy level does not limit reading.[^18] The details are in [Permissions and autonomy](https://commandmail.app/en/docs/permissions-and-autonomy).

Command Mail treats email content as untrusted data and flags suspected prompt injection. A flag is no guarantee that every attempt is caught. Command Mail blocks agents from writing on their own to senders, mailing lists and no-reply addresses it recognizes as automated; that recognition is incomplete as well.[^14][^18]

### Sending from forwarded addresses

A forwarded address can send from Command Mail once you set up a route for it. You do that per address in Settings under Connections, in the app only; an agent cannot do it for you. There are two routes (code `outbox.ts` and settings texts, commit `15af567`):

- **Through your mail provider (SMTP).** You add an app password once, Command Mail signs in to check it and then sends through your provider's outgoing server. Recipients see your address.
- **Through Command Mail (relay).** No password. After a confirmation code sent to your address, mail leaves from a Command Mail address with your name, and replies go to your address via Reply-To.

Outlook.com and Hotmail accept no app passwords for sending, so the relay is the only route there. Recipients then see a Command Mail address instead of your Outlook address, much like Shortwave, where the reply comes from the Gmail address.[^2] A custom domain you have proved with a DNS record and set up for sending needs neither route (`domains.ts`, `maySendFrom`).

Sending from Command Mail requires Pro; Free does not send at all.[^14] Autonomy levels, the daily agent limit and the block on writing to automated senders apply to both routes alike. We have not tested the routes ourselves with Outlook.com or iCloud.

### Microsoft 365 has to allow forwarding

Microsoft 365 organizations can block automatic forwarding to external addresses. Microsoft says the behavior of the default setting, "Automatic - System-controlled", depends on the organization: for new organizations it has meant "Off" since 2021, and Microsoft recommends setting "On" or "Off" explicitly. When the policy blocks forwarding, the sender receives a non-delivery report with code `5.7.520`.[^8] Before forwarding a work mailbox to Command Mail, check with whoever runs your tenant. Without that permission nothing arrives.

### Pricing

You can start for free with one mailbox, the last 90 days, search, sorting, the morning brief and drafts, but no sending. Pro is €19 a month for the first 100 paying Pro accounts for as long as the subscription runs, then €29 a month, and adds sending, up to ten mailboxes and full history. You can try Pro for 7 days for €1.[^14]

## When Shortwave is the better choice

Stay with Shortwave if your mail already lives in Gmail or Google Workspace and you do the work yourself in the client. The assistant sits in the inbox, understands "this email" on screen, writes in your tone and reaches tools like HubSpot or Notion over MCP.[^7][^5] Because Shortwave syncs with Gmail, archiving or deleting there shows up in Gmail.[^6]

Command Mail works on forwarded copies. Archiving or deleting in Command Mail does not reach your Gmail account.[^16] For a polished client with team features, read statuses and calendar integration, Shortwave is the better fit.[^3]

## When Command Mail fits

Command Mail fits when an agent should do most of the work and your addresses are spread out: a work address on Microsoft 365 where forwarding is allowed, an old iCloud address, a personal Gmail account. The agent sees all of it in one place, files mail by rules you define, prepares a morning brief with deadlines and open replies, and drafts answers for your approval.[^16]

It also fits when you want to choose the agent yourself. Claude, ChatGPT, Codex or a custom agent through the CLI all work against the same mailbox with the same permissions.[^14] For several addresses, see [Multiple email accounts with one AI agent](https://commandmail.app/en/guides/multiple-email-accounts-ai-agent).

## When Command Mail is the wrong choice

Command Mail is built for working with an agent. Our documentation does not list the conveniences Shortwave offers heavy writers, such as read statuses or link tracking.[^3][^16] Changes do not flow back to the original mailbox. If you want to send from an Outlook.com address and recipients must see exactly that address as the sender, the relay will not get you there.

We cannot show SOC 2 or ISO 27001 certification for Command Mail. The operator is FYN Labs LLC in the United States; the app and database run on Cloudflare.[^17]

## Switching from Shortwave to Command Mail

You can try Command Mail without cancelling Shortwave. Command Mail receives copies, so your Gmail account and Shortwave stay as they are.[^16]

1. Create an account at commandmail.app with Google, Apple or email.
2. Add a mailbox in Settings under "Connect mailbox"; Command Mail shows its private intake address.[^16]
3. Turn on forwarding at your provider: in Gmail under "Forwarding and POP/IMAP", in Outlook.com under Settings, Mail, Forwarding.[^2] For Microsoft 365, confirm first that external forwarding is allowed.[^8]
4. Connect your agent, for example in Claude Code with `claude mcp add --transport http commandmail https://commandmail.app/mcp`.[^14]
5. Grant only `mail:read` and `mail:draft` at first and add sending later.
6. Optionally import older mail as MBOX or EML through the CLI. An import is a one-time copy.[^16]

To check the setup, send a test email and look for it in the right mailbox, then confirm that the agent's first `capabilities` call lists your account, its permissions and your mailboxes.[^14]

## Which option for whom

- **Everything in Google Workspace, working in the client:** stay with Shortwave.[^1]
- **Outlook and Gmail in one client, agent over MCP:** Superhuman on Business.[^9][^10]
- **Many email accounts, free to start:** Spark.[^11]
- **Exchange and IMAP explicitly documented, low yearly price:** Canary.[^13][^12]
- **Your own agent across addresses at several providers, permissions per connection:** Command Mail.[^14]

As of 2026-10-23. The statements about sending from Command Mail are based on the app code at commit `15af567` (`outbox.ts`, `domains.ts`, settings texts). We have not run our own tests with Shortwave.[^1]

If you want to try Command Mail, start for free at [commandmail.app](https://commandmail.app/login?signup=1) and connect your agent afterwards.

## Frequently asked questions

### Can I use Shortwave without a Gmail account?

No. Shortwave requires a Gmail or Google Workspace account to sign in. Other addresses are forwarded to that account; a free Gmail account works as the bridge.

### Does Shortwave work with Microsoft 365 or Exchange?

Not according to Shortwave's help page on 2026-10-23. Microsoft 365 and Exchange are not supported at this time, and Shortwave gives no timeline. Outlook.com, Hotmail and Live work through forwarding only, without sending from that address.

### Can an outside agent such as Claude or ChatGPT reach my Shortwave mailbox?

We found no MCP server that Shortwave offers to outside agents. Shortwave acts as an MCP client: its built-in assistant calls other services over MCP, on Business plans and above, in beta.

### Can Command Mail send from my Outlook.com or iCloud address?

On Pro, once you set up sending for that address in Settings under Connections. An iCloud address sends through Apple's SMTP server with an app-specific password, and recipients see your address. Outlook.com and Hotmail accept no app passwords; there Command Mail sends from its own relay address and replies go to your Outlook address via Reply-To.

### What if my Microsoft 365 organization blocks external forwarding?

If the outbound spam policy blocks automatic forwarding, nothing reaches Command Mail, and the sender gets a non-delivery report with code 5.7.520. External forwarding has to be allowed by whoever administers the Microsoft 365 tenant.

## Sources

1. [Shortwave: Use Shortwave with other email providers](https://www.shortwave.com/docs/how-tos/microsoft-outlook-exchange-other-sign-in-support/), accessed 2026-10-23
2. [Shortwave: Unified inbox via forwarding](https://www.shortwave.com/docs/how-tos/unified-universal-inbox-support/), accessed 2026-10-23
3. [Shortwave: Pricing](https://www.shortwave.com/pricing/), accessed 2026-10-23
4. [Shortwave: Billing](https://www.shortwave.com/docs/guides/billing/), accessed 2026-10-23
5. [Shortwave: Using MCP with Shortwave](https://www.shortwave.com/docs/how-tos/using-mcp/), accessed 2026-10-23
6. [Shortwave: Security & Privacy](https://www.shortwave.com/docs/guides/security/), accessed 2026-10-23
7. [Shortwave: The Shortwave AI Assistant](https://www.shortwave.com/docs/guides/ai-assistant/), accessed 2026-10-23
8. [Microsoft Learn: Control automatic external email forwarding in Microsoft 365](https://learn.microsoft.com/en-us/defender-office-365/outbound-spam-policies-external-email-forwarding), accessed 2026-10-23
9. [Superhuman: Pricing Plans (Help Center)](https://help.superhuman.com/hc/en-us/articles/46178817646861-Pricing-Plans), accessed 2026-10-21
10. [Superhuman: Superhuman Mail MCP Server (Help Center)](https://help.superhuman.com/hc/en-us/articles/46005696690317-Superhuman-Mail-MCP-Server), accessed 2026-10-21
11. [Spark Mail: Pricing](https://sparkmailapp.com/pricing), accessed 2026-10-23
12. [Canary Mail: Pricing](https://canarymail.io/pricing), accessed 2026-10-23
13. [Canary Mail: AI](https://canarymail.io/ai), accessed 2026-10-23
14. [Command Mail: llms.txt (pricing, permissions, connection)](https://commandmail.app/llms.txt), accessed 2026-10-23
15. [Command Mail: For agents](https://commandmail.app/en/agents), accessed 2026-10-23
16. [Command Mail: Documentation](https://commandmail.app/en/docs), accessed 2026-10-23
17. [Command Mail: Privacy, operator and hosting](https://commandmail.app/privacy), accessed 2026-10-23
18. [Command Mail: Permissions and autonomy](https://commandmail.app/en/docs/permissions-and-autonomy), accessed 2026-10-23

[^1]: [Shortwave: Use Shortwave with other email providers](https://www.shortwave.com/docs/how-tos/microsoft-outlook-exchange-other-sign-in-support/), accessed 2026-10-23
[^2]: [Shortwave: Unified inbox via forwarding](https://www.shortwave.com/docs/how-tos/unified-universal-inbox-support/), accessed 2026-10-23
[^3]: [Shortwave: Pricing](https://www.shortwave.com/pricing/), accessed 2026-10-23
[^4]: [Shortwave: Billing](https://www.shortwave.com/docs/guides/billing/), accessed 2026-10-23
[^5]: [Shortwave: Using MCP with Shortwave](https://www.shortwave.com/docs/how-tos/using-mcp/), accessed 2026-10-23
[^6]: [Shortwave: Security & Privacy](https://www.shortwave.com/docs/guides/security/), accessed 2026-10-23
[^7]: [Shortwave: The Shortwave AI Assistant](https://www.shortwave.com/docs/guides/ai-assistant/), accessed 2026-10-23
[^8]: [Microsoft Learn: Control automatic external email forwarding in Microsoft 365](https://learn.microsoft.com/en-us/defender-office-365/outbound-spam-policies-external-email-forwarding), accessed 2026-10-23
[^9]: [Superhuman: Pricing Plans (Help Center)](https://help.superhuman.com/hc/en-us/articles/46178817646861-Pricing-Plans), accessed 2026-10-21
[^10]: [Superhuman: Superhuman Mail MCP Server (Help Center)](https://help.superhuman.com/hc/en-us/articles/46005696690317-Superhuman-Mail-MCP-Server), accessed 2026-10-21
[^11]: [Spark Mail: Pricing](https://sparkmailapp.com/pricing), accessed 2026-10-23
[^12]: [Canary Mail: Pricing](https://canarymail.io/pricing), accessed 2026-10-23
[^13]: [Canary Mail: AI](https://canarymail.io/ai), accessed 2026-10-23
[^14]: [Command Mail: llms.txt (pricing, permissions, connection)](https://commandmail.app/llms.txt), accessed 2026-10-23
[^15]: [Command Mail: For agents](https://commandmail.app/en/agents), accessed 2026-10-23
[^16]: [Command Mail: Documentation](https://commandmail.app/en/docs), accessed 2026-10-23
[^17]: [Command Mail: Privacy, operator and hosting](https://commandmail.app/privacy), accessed 2026-10-23
[^18]: [Command Mail: Permissions and autonomy](https://commandmail.app/en/docs/permissions-and-autonomy), accessed 2026-10-23

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Command Mail: one inbox for you and your AI agent. Start free: https://commandmail.app/login?signup=1 · Connect your agent: https://commandmail.app/en/agents · MCP: https://commandmail.app/mcp