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Head-to-head · AI Email Assistants

MailMaestro vs Shortwave

  • Updated Oct 2026
  • Both researched from official sources
  • 7 checks side by side
Higher score MailMaestro #5 in AI Email Assistants 8.4/10 Free plan · 14-day trial Free planFree trial✓ 4 of 5 features Visit MailMaestro
Shortwave #6 in AI Email Assistants 8.3/10 Free plan · 14-day trial Free planFree trial✓ 0 of 5 features Visit Shortwave

MailMaestro leads on 1 check, Shortwave on 0, and 6 are even. Who comes out ahead on the 7 yes/no, price and count checks where we have data for both products. The editor score weighs everything else too.

Our verdict

  • Highest scoreMailMaestro · 8.4/10
  • Lowest starting priceMailMaestro · $12/seat/mo
  • Free planboth
  • Free trialboth
  • Most featuresMailMaestro · 4 of 5

MailMaestro scores higher on our rubric for ai email assistants: 8.4 against 8.3 out of 10; our editors rank them #5 and #6.

MailMaestro is cheaper to start at $12/user/mo against $30/user/mo.

MailMaestro is the better fit for outlook and Gmail users wanting focused AI help. Shortwave is the better fit for AI Gmail workflows with team collaboration.

  • MailMaestro fits best

    Outlook and Gmail users wanting focused AI help

  • Shortwave fits best

    AI Gmail workflows with team collaboration

Advertiser disclosure: iTechGuides is reader-supported. Vendors can pay for top positions in our rankings and for a place on other products' pages, and we may earn a commission when you click some links. Bought places stand at the number bought; this page and our disclosure say so. Paying vendors may get a fuller, more detailed review from our editors, and that review can change their score. How we rank.

Side by side

Feature MailMaestro 8.4/10 Visit ↗ Shortwave 8.3/10 Visit ↗
At a glance
Editor score 8.4 8.3
Ranking #5 in AI Email Assistants #6 in AI Email Assistants
Best for Outlook and Gmail users wanting focused AI help AI Gmail workflows with team collaboration
Pricing model Free plan + paid Free plan + paid
Starting price $12/seat/mo (best) $30/seat/mo
Free plan ✓ ✓
Free trial 14 days 14 days
Free trial length 14 days 14 days · no card needed
Deployment Cloud, Browser extension Cloud, Desktop, Mobile
Platforms Web, Chrome extension Web, Windows, macOS, iOS, Android
Integrations 5 integrations 7 integrations
Features MailMaestro 4/5 · Shortwave 0/5
Inbox triage ✓ (best) Not checked yet
AI reply drafting ✓ (best) Not checked yet
Automatic sending — Not checked yet
Thread summaries ✓ (best) Not checked yet
Follow-up actions ✓ (best) Not checked yet
Specs
Email platforms Not checked yet Not checked yet
Our review
Pros
  • Drafts and improves messages using conversation context and tone controls
  • Summarizes email threads and attachments, with reminders and inbox triage
  • Connects with Outlook, Gmail, and their calendars for meeting responses
  • Combines AI search, writing, autocomplete, summaries, and attachment analysis
  • Supports inbox organization, scheduling, calendar tools, and multiple accounts
  • Team features include thread sharing, comments, and assignments
Cons
  • Free plan limits compose, reply, and improve requests to three per week
  • Auto-send is not included
  • Enterprise features include custom integrations and data retention
  • Direct sign-in requires Gmail or Google Workspace accounts
  • Other providers generally require forwarding through Gmail
  • Paid monthly plans start at $30 per seat
Our verdict

MailMaestro is an AI email assistant for professionals who want help composing, refining, and replying to messages, as well as organizing an inbox. It works with Microsoft Outlook and offers Gmail through a Chrome extension. Drafts can use…

Read the review →

Shortwave is an AI-powered email client built for Gmail and Google Workspace accounts, serving individuals and teams that want email organization, AI assistance, and collaboration in one workflow. Its capabilities include AI-powered search…

Read the review →
  1. MailMaestroAI Email Assistants 8.4Free plan · 14-day trial
  2. ShortwaveAI Email Assistants 8.3Free plan · 14-day trial

Strengths and trade-offs

  • MailMaestro — where it wins

    • Drafts and improves messages using conversation context and tone controls
    • Summarizes email threads and attachments, with reminders and inbox triage
    • Connects with Outlook, Gmail, and their calendars for meeting responses

    Where it doesn't

    • Free plan limits compose, reply, and improve requests to three per week
    • Auto-send is not included
    • Enterprise features include custom integrations and data retention

  • Shortwave — where it wins

    • Combines AI search, writing, autocomplete, summaries, and attachment analysis
    • Supports inbox organization, scheduling, calendar tools, and multiple accounts
    • Team features include thread sharing, comments, and assignments

    Where it doesn't

    • Direct sign-in requires Gmail or Google Workspace accounts
    • Other providers generally require forwarding through Gmail
    • Paid monthly plans start at $30 per seat
  • MailMaestro8.4/10 · Free plan · 14-day trial

    Draft, refine, summarize, and organize email with AI across Outlook and Gmail.

    Visit MailMaestroFull verdict →
  • Shortwave8.3/10 · Free plan · 14-day trial

    An AI-focused Gmail client with team workflows and a free plan; paid tiers start at $30 per seat monthly.

    Visit ShortwaveFull verdict →

More comparisons

All AI email assistants comparisons → · Full ranking →

Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026

Last updated · How we research and update