MailMaestro review

MailMaestro is an AI assistant that sits inside Outlook through the Microsoft Marketplace and inside Gmail through a Chrome extension, and the Flowrite site now says Flowrite is MailMaestro. The Email plan, at $12 per seat a month billed annually, writes, replies to and improves emails, runs unlimited AI agents that label, draft and follow up, and summarizes long threads. Adding TeamsMaestro meeting notes as the MaestroDuo bundle costs $25 per seat a month billed annually at $300 a year, which the vendor says saves $48 compared with buying both. A free plan remains after the 14-day trial of Pro. Maestro Labs lists SOC 2 Type II, GDPR and HIPAA compliance and says your data is never used to train AI models, which matters for legal, finance and HR teams. Annual plans are not refundable, so try the monthly plan first if unsure. For people who do not want to switch email clients, it is the strongest add-in we compared at this price.

Who it is for

people who want to keep Outlook or Gmail

Price

Free plan; Email $12 per seat a month billed annually; MaestroDuo with meeting notes $25 per seat a month billed annually.

Email $12 per seat/month
Quoted from the vendor pricing page on November 13, 2026.

Key features

• Writes, replies to and improves emails inside Outlook and Gmail
• Unlimited AI agents that label, draft and follow up
• Summaries of long emails and threads
• Optional TeamsMaestro meeting notes in 40+ languages
• SOC 2 Type II, GDPR and HIPAA compliance

Strengths and weaknesses

• Strength: Free plan stays available after the 14-day trial
• Strength: Works where people already write, with an Outlook add-in and a Chrome extension for Gmail
• Strength: Maestro Labs says customer data is never used to train AI models
• Weakness: Annual plans are not refundable after purchase
• Weakness: Meeting notes cost extra unless you buy the $25 MaestroDuo bundle
• Weakness: Single sign-on is reserved for Enterprise deals of 100+ seats

Key facts

• Free plan: Yes, kept after the trial
• Free trial: 14 days on MailMaestro Pro
• Works in: Outlook and Gmail
• Annual discount: 20% on MailMaestro

Where it ranks

MailMaestro is No. 2 in our Best AI Email Writers verdict.