If Outlook is starting to feel like a never-ending to-do list, you’re not imagining it. Between long email threads, missed follow-ups, and the mental load of keeping track of it all, your inbox can slow you down fast.
That’s where AI email assistants come in. Tools like Lindy, MailMaestro, and Superhuman offer different ways to get ahead — from fast drafting and cleanup to deeper automation and context-aware replies.
In this review, we’ll cover:
- The top 7 Outlook AI assistants
- Pricing, features, pros, and cons of each tool
- Use cases across writing, summarizing, and organizing
- A side-by-side comparison table
- How we tested and evaluated these tools
Let’s start with a quick look at the 7 tools we reviewed.
The 7 best Outlook AI assistants: TL;DR
Each of these tools brings something unique to the table depending on how you use email at work. Here’s a quick overview of the top Outlook AI tools we reviewed:
- Lindy – Best for automating full email workflows (not just replies)
- MailMaestro – Best for fast, tone-aware executive communication
- Superhuman AI – Best for power users who prioritize speed
- ChatGPT Add-in for Outlook – Best for custom, prompt-based email drafting
- Clean Email AI – Best for inbox cleanup and rule-based filtering
- Copilot – Best for deep Microsoft 365 integration
- Otter.ai – Best for auto-follow-ups after meetings
Next, we explore them in detail.
1. Lindy – Best for automating workflows around emails
Lindy is a no-code AI automation platform that integrates with Outlook. It acts as an email AI assistant to help users automate email-related workflows across business tools.
It supports 7,000+ integrations across 1,600+ apps, and connects with your CRM, calendar, and project management tools to write emails and complete related actions.
Lindy can automate your entire email workflow, triaging your inbox, sending messages or follow-ups, and recording them in your CRM. It can even schedule meetings and takes action across your systems.
It’s perfect for sales reps, support managers, and entrepreneurs who manage complex, high-volume email workflows.
Features
- Reads email context to draft replies automatically
- Prioritizes and triages your inbox, including smart flagging and deferrals
- Handles multi-step workflows like following up after meetings or assigning tasks
- Customizable AI agents for scheduling, lead routing, note-taking, or form handling
- Integrates with thousands of apps, including Notion, Google Calendar, and ClickUp
- Security built in with SOC II and HIPAA compliance
- Supports multi-language workflows via phone agents
- Hundreds of ready-to-use, customizable templates for sales, support, recruiting, and more
Pros
- Automates more than just writing, helps with business operations
- Great for small, high-output teams juggling lots of tools
- Powerful cross-app coordination between email, CRM, and calendars
Cons
- Takes a bit more setup than simple drafting tools
- Can feel like overkill if all you want is smarter replies
Pricing
- Starts free, with 400 credits/month
- Pro plan: $49.99/month for 5,000 credits
- Business plan: $299.99/month for 30,000 credits
- Enterprise: Custom pricing
{{templates}}
2. MailMaestro – Best for fast, tone-aware executive communication
MailMaestro is an AI writing assistant built specifically for Outlook. It helps professionals draft clear, formal, and well-toned business emails in seconds, directly inside their inbox.
The assistant can summarize long threads, rewrite drafts with different tones, and generate new emails based on context. It’s available as an Outlook add-in and works especially well for executives or managers who need to respond quickly without sounding rushed or robotic.
MailMaestro includes fine-tuned tone presets like concise, formal, assertive, or friendly. It also integrates lightly with calendars and offers features to rephrase, summarize, or autofill based on email history, all from a minimal, fast-loading side panel.
Features
- Tone rewriting –– formal, concise, assertive, and more
- Summarizes long threads before drafting
- One-click email generation based on context
- Multi-language support
- Works as an Outlook add-in, no extra tools required
Pros
- Sharp tone controls for business settings
- Easy to install and use directly in Outlook
- Lightweight and minimal interface
Cons
- Doesn’t automate workflows or cross-tool tasks
- Best suited for drafting, not broader task execution
Pricing
- Starts free, but no valuable email capabilities
- Professional: $20/user/month, billed monthly
- Enterprise: Custom pricing
3. Superhuman – Best for power users who prioritize speed
Superhuman is an email client that now supports Outlook alongside Gmail. It’s built for people who live in their inbox and want to move through messages as fast as possible, with AI features layered into a sleek, shortcut-first interface.
Superhuman’s AI assistant helps users summarize long threads, draft replies, and rephrase emails based on tone or intent. But where it shines is its speed — think split inboxes, blazing-fast keyboard shortcuts, and a command bar that keeps your hands off the mouse.
It’s ideal for founders, execs, or sales reps who manage high email volume and value efficiency above all else.
Features
- AI-powered email drafting and rephrasing
- Summarizes long threads at a glance
- Command bar and deep keyboard shortcut support
- Split inbox, read tracking, and snoozing
- Now available for Outlook users via desktop client
Pros
- Fastest inbox experience for high-volume users
- Clean, minimal interface with power-user controls
- Built-in AI helps polish replies without slowing you down
Cons
- Requires learning new shortcuts and the interface
- Not built for task automation or tool integrations
Pricing
- Starter: $30/user/month, billed monthly
- Business: $40/user/month, billed monthly
- Enterprise: Custom pricing
4. ChatGPT Add-in for Outlook – Best for custom, prompt-based email drafting
The ChatGPT Add-in for Outlook integrates OpenAI’s language model directly into Microsoft Outlook, enabling users to craft custom prompts for summarizing, drafting, or analyzing emails.
Designed for those comfortable with prompt engineering, it offers a flexible approach to email management within Outlook. It’s ideal for professionals who want to tailor AI responses to specific workflows. Users can manage multiple configurations for different scenarios, enhancing productivity and email handling efficiency.
Features
- Custom prompt-based email drafting
- Summarization of threads and messages
- Processing of specific email sections
- Manages multiple configurations for varied scenarios
- AI-generated output in a separate panel for easy comparison
Pros
- Highly customizable to fit unique workflows
- Supports multiple OpenAI models, including GPT-4o
- Free to use with your own OpenAI API key
Cons
- Requires manual setup and familiarity with prompt engineering
- No built-in CRM or third-party app integrations
- Not designed for inbox triage or workflow automation
Pricing
- Free to use, requires an OpenAI API key
- For enterprises, a fixed price of £4,000 or less
5. Clean Email – Best for inbox cleanup and rule-based filtering
Clean Email is a productivity tool built to help users organize and declutter their inbox, rather than draft or respond to emails. Its AI email assistant focuses on applying smart filters, bulk actions, and automation rules to keep your Outlook inbox manageable.
It’s helpful for users who deal with a flood of newsletters, promotions, or internal threads and want to automate how those emails are grouped, labeled, or deleted. The tool works with Outlook through IMAP integration and is designed to run quietly in the background once set up.
It best suits professionals who want to focus only on the emails that matter.
Features
- Smart filters by sender, keywords, categories
- One-click unsubscribe and block options
- Prebuilt automation rules for inbox organization
- Auto-archive and thread grouping
- Works across Outlook, Gmail, and other providers
Pros
- Great for decluttering without deleting important emails
- Low maintenance once rules are set up
- Privacy-first approach — doesn’t read email content
Cons
- Doesn’t assist with email drafting or replying
- Not suitable for complex workflows or task automation
Pricing
- For one account: $9.99/month
- For 5 accounts: $19.99/month
- For 10 accounts: $29.99/month
6. Copilot – Best for deep Microsoft 365 integration
Copilot is Microsoft’s native AI assistant built into the 365 suite, including Outlook. It uses Microsoft’s large language model in partnership with OpenAI to help draft emails, summarize long threads, suggest replies, and surface relevant information from your docs, calendar, or Teams messages — directly inside the Outlook interface.
Once enabled, Copilot works alongside you as you write, offering suggestions or drafting emails from scratch based on meeting recaps, project documents, or past conversations.
This tool is ideal for organizations already on Microsoft 365 and are looking for an AI layer that fits directly into existing workflows.
Features
- Inline drafting and rewriting assistance
- Thread summarization with action item detection
- Pulls context from Word, Excel, Teams, SharePoint, and more
- Built directly into Outlook desktop and web apps
Pros
- Tailored for Microsoft 365 users
- Tightly integrated with calendar, docs, and Teams
- No separate installation or add-ons needed
Cons
- Only available with enterprise Copilot license
- Limited customization or prompt-level control
Pricing
- Free on web or the app with limited daily usage
- Pro plan from $20/user/month
7. Otter.ai – Best for auto-follow-ups after meetings
Otter.ai is a meeting assistant that connects with your email to automatically generate follow-up emails based on your meeting transcripts. It’s not a traditional Outlook AI assistant, but it connects the dots between what’s said in a call and what needs to be followed up on over email.
After a Zoom, Google Meet, or Microsoft Teams call, Otter.ai creates a summary and drafts a follow-up message that you can copy into Outlook or send manually. It also detects the next steps and action items, making it useful for sales teams, consultants, and internal project leads who run multiple meetings each week.
Features
- Real-time meeting transcription
- Automatic follow-up email drafts based on notes
- Action item detection and smart summaries
- Works with Zoom, Teams, and Meet
Pros
- Saves time on manual note-taking and follow-ups
- Great for recurring client or team calls
- Integrates directly with video conferencing platforms
Cons
- Doesn’t plug directly into Outlook for email sending
- No inbox management or reply automation
Pricing
- Free plan available
- Pro: $16.99/user/month, billed monthly
- Business: $30/user/month, billed monthly
Next, we compare these tools for a glanceable overview.
Top Outlook email assistants: at a glance
We created a summary table to quickly compare all seven tools — their strengths, pricing, and setup. Here’s how they stack up side-by-side:
A lot of thought went into compiling this list. We explain that next.
How we reviewed the best Outlook AI assistants
To find the best AI assistants for Outlook, we reviewed each one in an email workflow. We didn’t just focus on the features, but saw how well they fit into the day-to-day of using Outlook at work.
Each tool was evaluated for setup time, accuracy of its outputs, and how well it handled core tasks like drafting, summarizing, and follow-ups. The best Outlook AI assistant in 2025 should:
- Draft smart, context-aware replies
- Plug directly into Outlook — no janky workarounds
- Automate common actions like follow-ups, summaries, or delegation
- Be usable in business workflows — not just personal inboxes
Evaluation criteria
We chose 4 key criteria of evaluation. They were:
- Ease of setup and integration: Can a user get started in under 10 minutes? Is it available as an Outlook add-in or built-in tool?
- Core features tested: Can it draft replies, summarize long threads, rewrite tone, and suggest follow-ups?
- Accuracy and usefulness of outputs: Were the responses usable as-is, or did they need heavy editing?
- Productivity impact: How many manual steps were removed from the email process?
Some tools like Superhuman and MailMaestro stood out for being fast and focused. Others like Lindy or Copilot offered deeper functionality by integrating with other work apps.
Let’s move to the Outlook AI email assistant and define it next.
What is an Outlook AI email assistant?
An Outlook AI email assistant is a tool that uses artificial intelligence to help you manage email-related tasks faster — like writing replies, summarizing threads, or organizing your inbox.
Most assistants work as Outlook add-ins or integrations. Some are built into the Outlook experience (like Microsoft Copilot), while others connect through browser extensions or external dashboards.
Their goal is simple –– to reduce the time you spend inside your inbox without missing anything important.
So, how can these assistants help teams? We answer that next.
What can an AI email assistant help you do?
They can help you do many things and save hours every week. Here’s how they help:
- Reply suggestions: Drafts personalized responses based on previous messages or thread context.
- Inbox cleanup: Automatically filters, tags, and archives non-urgent emails, so your inbox stays focused.
- Follow-up automation: Sends reminders or auto-generated nudges after meetings or unanswered emails.
- Email generation from prompts: Write entire emails from scratch using short instructions or templates.
In addition to Outlook capabilities, some tools also extend their capabilities across other platforms. For example, a few AI assistants can log follow-ups into your CRM, schedule meetings, or pull key details from documents, all from inside your email workflow.
Next, we’ll cover the features and capabilities that you should look for in an Outlook AI assistant.
{{cta}}
Features to look for in an Outlook AI assistant
Some email assistants are just writing tools in a sidebar. The good ones automate meaningful tasks tied to your calendar, CRM, or team.
Here are the features that matter most if you’re evaluating AI tools for work:
Outlook compatibility
Look for native Outlook add-ins or integrations that don’t require a separate interface or copy-pasting between tools. Bonus points for desktop and web compatibility.
Smart reply and summary capabilities
The best assistants understand the context — like what was said in the last few emails, who’s involved, and what’s being asked. Based on that, they suggest replies or generate summaries that sound human.
Calendar and CRM integrations
Tools that connect with Google Calendar, Microsoft 365, Salesforce, HubSpot, or Notion make it easier to remain in sync with your emails without switching tabs. Some even log calls or pull in meeting notes.
If you work in sales or operations, these connections often matter more than the writing itself.
Tone, formatting, and personalization controls
Useful assistants let you adjust tone to be more formal or friendly, auto-format bulleted lists or headers, and personalize based on name, company, or previous conversation history.
If you’re still manually tweaking every AI draft, it’s not saving you time.
Security and privacy compliance
For users in regulated industries like healthcare or legal, look for tools that are SOC 2 or HIPAA-compliant. They must encrypt user data, and not use your emails to train their models. Tools like Lindy and Clean Email make privacy a core feature, not an afterthought.
Frequently asked questions
What’s the best AI assistant for Outlook?
Lindy offers more flexibility if you're looking for broader automation across CRMs and calendars. Tools like MailMaestro or Superhuman are strong AI email assistant picks if you want fast drafting with tone control.
How do I add an AI assistant to Outlook?
Most tools are available as Outlook add-ins through Microsoft AppSource. For example, you can install MailMaestro, Clean Email, or ChatGPT-based tools as plugins in just a few clicks. Others, like Otter.ai, work externally and complement your inbox instead.
Can AI reply to emails for me?
Yes, AI can reply to emails for you. Nearly all the tools in this list can generate replies using thread context or prompt-based instructions. Tools like ChatGPT or Copilot offer suggested drafts. Lindy can generate responses based on attached documents, CRM data, or recent meetings.
Is AI safe for business email?
Most AI tools today are safe for business email. Look for tools with SOC 2, HIPAA, or GDPR compliance, especially if you work in healthcare, legal, or enterprise environments. Clean Email and Lindy, for example, prioritize user privacy and don't train models on your data.
What’s the difference between ChatGPT and Lindy?
ChatGPT helps you write. You give it a prompt, and it drafts a reply or summary, one email at a time. Lindy reads the context of your inbox, tracks past threads, understands what’s already been said, and acts accordingly.
It goes beyond writing and can tag, triage, update your CRM, and even follow up automatically, without you needing to prompt it each time.
Try Lindy, your Outlook AI email assistant and workflow automation tool
If you’re looking for an easy-to-use AI solution that helps you better organize and manage your inbox while also providing automations around emails, meetings, and sales, go with Lindy.
Out of all the AI email assistants, here’s why Lindy may suit you the best:
- Simple no-code interface: You won’t need coding, programming, or technical skills to create your automations with Lindy — it offers a drag-and-drop visual workflow builder.
- AI agents customized to your needs: You can make versatile AI agents that understand plain English and accelerate your productivity in many ways. For instance, create an assistant that bolsters your sales funnel by finding leads from websites and business intelligence sources like People Data Labs. Create another agent that sends out emails to each lead and schedules meetings with members of your sales team.
- Affordability: Build your first few automations with Lindy’s free version and get up to 400 tasks. With the Pro plan, you can automate up to 5,000 tasks, which offers much more value than Lindy’s competitors.
%20(1).png)
%20(1).png)
.png)
.jpg)
.png)
