Beyond Mail Filters: Wino Mail 2.1 Beta

On August 3, I released Mail Filters as a beta feature. I expected the next stretch of work to be mostly about polishing filters and preparing another update.

It became something much bigger.

Since that beta, Wino Mail has grown beyond the inbox. Version 2.1 introduces a complete People experience, a new To Do mode, the Wino Intelligence add-on, a redesigned message-list experience, much deeper personalization, and much more. It also changes how Wino is packaged and distributed so the Store, beta, and sideloaded editions can have clearer identities and update paths.

This is the largest step forward for Wino Mail so far. This version has full Native AOT for x86,x64 and ARM64 devices as well. Bringing extreme performance available for Windows apps today. Nothing should feel laggy.

The headlines

• People is now a complete contact-management experience, with account-backed contacts, address books, lists, favorites, photos, search, and a much richer editor.
• To Do joins Mail, Calendar, and People as a first-class mode, bringing task lists, smart views, due dates, reminders, steps, and synchronized tasks into Wino.
• The paid Wino Intelligence add-on makes the inbox easier to understand, with meaning-based search, message insights, summaries, translation, rewriting, and Daily Briefing.
• The mail experience has been substantially refined, including Reader View, a new searchable mail context flyout, completely reworked hover actions, a better search bar, faster loading, and clearer visual feedback.
• Accounts are easier to recognize and manage, with account profile pictures and one consistent account menu throughout Mail, Calendar, People, and To Do.
• Personalization goes much further, with a theme gallery and editor, live message-list previews, and more control over how actions and content appear.
• Upgrading is safer and clearer, with a dedicated migration experience designed to preserve progress and recover cleanly if an upgrade is interrupted.
• Release infrastructure has been rebuilt, preparing distinct Store, beta, and stable sideload channels with clearer identities and update paths.

People: contacts finally have a proper home

People is not a small contacts popup added beside the inbox. It is a new top-level Wino mode built for managing contacts across accounts.

The new People page brings contacts from supported accounts into one consistent experience. You can browse all contacts, narrow the view to favorites, switch between address books and personal lists, or search directly for a person. Contact counts and grouped views make larger collections easier to understand, while account indicators help preserve context when several providers are connected.

The contact editor has also been rebuilt. Instead of stopping at a name and one email address, it can organize the details people actually keep: multiple email addresses and phone numbers, company and job information, postal addresses, websites, birthdays, personal notes, and list membership. Fields are grouped into clear categories so the editor remains approachable even when a contact contains a lot of information.

Profile pictures are now part of the full workflow. You can add, change, or remove a contact photo, and Wino uses those pictures throughout the People experience. Favorites are available as a quick filter, and a contact can be added to or removed from lists without duplicating the underlying person. You can also start a new email directly from a contact.

CardDAV received a much deeper rework alongside People. Wino can work with server-backed address books, create additional address books when the server allows it, and surface read-only or pending states more clearly. When the same contact changes both locally and on the server, Wino can present the conflict and let you keep the server version, keep your version, or preserve both. The goal is to make synchronization understandable instead of silently choosing for you.

People also behaves like a real Windows app entry. It has its own icon and activation route, so Wino can open directly into contacts rather than forcing every journey to begin in Mail.

To Do: tasks become a first-class Wino mode

Wino now includes a dedicated To Do experience alongside Mail, Calendar, and People.

The new mode is organized around task lists and familiar smart views such as My Day, Important, Planned, All, and Completed. You can create and rename lists, group them, choose colors, add tasks, and update them without waiting for a full refresh. Counts in the navigation keep the state of each view visible at a glance.

Individual tasks support the details needed for real planning: due dates, reminders, importance, notes, completion state, and smaller steps within a task. Completing an item gives immediate feedback, while synchronized changes are reconciled in the background. The interface is designed to stay responsive even while an account is updating.

To Do is integrated with the rest of Wino rather than living as a disconnected checklist. Dates can connect naturally with Calendar, and task data follows the capabilities granted to each account. Microsoft-backed tasks and supported synchronized accounts can participate alongside Wino's local task experience.

Wino Intelligence: Message analysis, translate, summary, rewrite and semantic search.

Wino Intelligence is the other major addition in this release. It is a paid, optional add-on intended to reduce the time spent searching, interpreting, and acting on mail. Mail, Calendar, People, To Do, and the rest of version 2.1 remain usable without purchasing the add-on.

The new Meaning search mode can find messages by intent rather than relying only on exact words. A search such as “the hotel booking for next week” can be useful even when those exact words never appear together in the message. Intelligence can work across the folders selected for each mailbox, and its management page shows coverage and progress so indexing is not an invisible background operation.

Inside a message, Intelligence can surface useful context such as priority, deadlines, whether a reply may be needed, and the kind of action involved. It can summarize a long message into key points, translate the content for reading, and keep the original available. In the composer, it can translate or rewrite a draft with a chosen tone or custom instruction before sending.

I'll share more details on a separate post. In this build you can see some visuals around this add-on but expect no working functionality for your account.

Daily Briefing

Daily Briefing turns important details from recent mail into a focused overview. It groups information by account and date, brings urgent or high-priority items forward, and recognizes practical follow-up actions. Depending on the message, that can mean opening the source email, replying, copying a verification code, or adding a date to Calendar.

Briefing items can be dismissed when they are not useful and shown again later through the ignored-items view. The experience covers recent days, not only the current moment, which makes it easier to recover something important after a busy day away from the inbox.

Intelligence is explicitly opt-in. Wino presents the privacy policy before processing selected mail data, lets each mailbox control its Intelligence coverage, shows add-on quota information, and provides controls to stop processing and delete Intelligence data. Intelligence entry points are hidden when the add-on is not active, so Wino remains uncluttered for people who do not use it.

A more capable mail experience

The inbox received a broad redesign while the new modes were being built.

Reader View

Reader View can turn a visually busy newsletter or heavily styled message into a cleaner reading layout. It extracts the meaningful content, removes much of the surrounding page furniture, and keeps the result inside Wino. The normal message remains available whenever the original formatting matters.

Message rendering now uses a lightweight in-memory path and shows a subtle loading placeholder instead of flashing blank content while switching between messages. Attachment recognition was unified for IMAP mail, improving the consistency of attachment indicators and presentation.

A new searchable mail context flyout and move dialog

The menu opened from a message has been replaced by a purpose-built mail context flyout. It gives commands clearer spacing, labels, icons, shortcut hints, section headers, and keyboard behavior while still feeling at home on Windows. It is designed to remain useful as Wino gains more commands instead of becoming an increasingly long generic menu.

The flyout is searchable. Start typing and Wino filters the commands immediately, making actions such as move, mark, flag, archive, or delete easier to reach without scanning the entire list. Moving mail is also much clearer: folders are displayed as a hierarchy, expandable groups behave like groups rather than destinations, and folder icons make similar names easier to distinguish.

Hover actions, rebuilt around the way you work

Hover actions are no longer a fixed row of three tiny targets. The entire experience has been rebuilt for more comfortable and predictable pointer use, with larger hit areas, stronger hover feedback, improved contrast, and placement that does not obscure the subject or sender.

The actions are now much more configurable. You can select None for slots you do not need and keep only one or two actions, choose small, medium, or large buttons, place them at several positions around the message row, and choose a slide, popup, or motion-free transition. The live preview in Message List settings shows the result before you return to the inbox. These changes directly respond to the request to make hover-action buttons easier to click.

The title-bar search box has also been rebuilt. It has clearer modes, improved history and cancellation behavior, and a more deliberate distinction between normal text search and Intelligence-powered meaning search.

Message-list personalization

The Message List settings page now includes a live preview, so density, layout, hover-action position, size, and animation can be evaluated before returning to the inbox. Mail templates were reorganized and tuned for faster cold loading, more stable grouping, and clearer alignment.

Keyboard shortcuts received a similar overhaul. Shortcuts are now organized by app mode, can cover actions such as creating a contact or task, reject unsafe key combinations, and can be reset to defaults as a group.

Account profile pictures and one consistent account menu

Accounts can now use real profile pictures throughout Wino instead of always being represented by a provider logo. Gmail and Outlook profile pictures can be retrieved from the provider, refreshed later, or replaced with a picture chosen on the device. A custom picture can also be removed at any time, returning the account to its normal provider icon. This is local only. Wino does not synchronize custom profile pictures to providers. If you had a custom color for the account circle will be wrapped with thin layer around the avatar.

The picture follows the account through the places where identity matters: the app shell, account selectors, merged-account views, settings, storage views, Daily Briefing, and other account-aware surfaces. This makes it much easier to distinguish two accounts from the same provider without repeatedly reading their addresses.

The account shell menus behind those pictures have also been unified. Mail, Calendar, People, and To Do now project accounts through the same visual and interaction model, with consistent icons, selection, expansion, context commands, and access to account settings. Capabilities still matter—an account only appears where it has granted the relevant mail, calendar, contacts, or task access—but the way users recognize and manage it no longer changes from one mode to another.

The shared menu work also improves merged and grouped accounts. Provider identity stays visible inside combined views, account-specific commands lead to the correct detail page, and synchronization controls describe the active mode rather than presenting a generic action with unclear scope.

Themes that feel personal

Wino's personalization settings now include a theme gallery and a full application-theme editor.

The gallery makes it easy to browse complete looks instead of configuring every color independently. The editor is for people who want more control: it provides a preview of the application surfaces while colors are adjusted, and recent refinements keep that preview useful during longer editing sessions. Theme behavior has also been tightened around app activation so an existing dark window does not briefly receive the wrong theme when opened from a notification.

Illustrations and account icons were refreshed across the application, including better colors in dark mode. Calendar account grouping, provider selection, the settings navigation, signed-out account pages, and the mode icons were also brought into the same visual system.

A safer upgrade to 2.1

The amount of data and configuration introduced during the beta required a more deliberate upgrade path.

Version 2.1 adds a dedicated migration window that explains progress instead of leaving the main app apparently stuck. Migration is resumable, so an interrupted upgrade can continue safely rather than starting from an uncertain state. Account setup and synchronization ordering were also adjusted so newly added accounts begin in a predictable order.

Users should notice the result, not the implementation: a clearer upgrade, less waiting without feedback, faster first loading of mail, and a much lower chance that an interruption leaves the app in an unusable state.

Release and distribution changes

The release pipeline has been rebuilt around three clearly defined distributions:

• Microsoft Store, for the normal Store-managed installation.
• Beta, for prerelease testing through its own signed package and App Installer feed.
• Stable sideload, for users and organizations that cannot use Microsoft Store.

The new model gives each distribution its own package identity and update profile. This means Store, beta, and stable sideload editions can coexist on the same computer instead of competing for the same installation. Beta builds can also carry distinct branding, making it much harder to confuse a test build with the stable app.

Both sideload channels use signed packages and App Installer update feeds. Release verification checks the package identity, included applications, architecture bundles, and signing result before an artifact is published. This is a major step toward answering the request for a stable installer outside Microsoft Store.

Smaller improvements worth mentioning

There are probably much more than I can think of right now, but here are the noticable ones.

• New Wino Editor control to handle message composing and rendering. Lighter, more capable and much faster. We'll have more control and do what users need from an advances mail composer in the future with this ground work.
• Settings search now understands more destinations and opens the relevant subpage more reliably.
• Account icons, provider selection, setup illustrations, and permission explanations have been refreshed.
• Calendar accounts are grouped more clearly, with better separation for ungrouped accounts.
• The sync button now reflects the active mode and the kind of data being synchronized.
• Signed-out Wino Account screens have been redesigned with clearer purchase and management states.
• Message loading now uses a shimmer placeholder to reduce visible flashing.
• Search, contact, task, and Intelligence screens received additional keyboard, screen-reader, automation, light-theme, dark-theme, and High Contrast work.
• Drafts are synchronized remotely silently when they are saved locally. Previously they were local only.
• Translations were refreshed across the supported language set for the new release.

Bugfixes

• Fixed an Outlook setup conflict that prevented users from adding an account when the Microsoft account's primary alias was already used by another Wino account. Wino now lets the user choose the correct mailbox address. #1016
• Fixed newly arrived Gmail and IMAP messages appearing in the middle of the message list until the folder was reloaded. #1023
• Fixed missing paperclip indicators for PDF and other attachments by unifying IMAP attachment recognition. #1018
• Fixed the expandable More row in the move menu being treated as if it were a destination folder. #1007
• Fixed account settings occasionally opening the wrong content when launched from an account in the sidebar. #959
• Fixed the Meaning search option remaining available when Wino Intelligence was not active. #1044
• Fixed double-clicking a word in the title-bar search box also maximizing or restoring the app window. #1036
• Improved IMAP connection testing, authentication compatibility, TLS handling, and certificate explanations for servers that previously failed during or immediately after sign-in. This includes the connection flow reported in #930.
• Fixed contact favorite and save actions after the People editor redesign.
• Fixed migrated IMAP task lists not being initialized correctly after upgrading.
• Fixed calendar virtualization issues that could cause incorrect or unstable month content while navigating.
• Fixed brief flashes and incorrect colors when returning to an existing dark-theme window.
• Fixed several semantic-indexing recovery and synchronization problems, including cases where Intelligence progress or results could become stale.
• Fixed release-only compatibility problems that prevented optimized builds from completing reliably.

Known Issues

As with every beta release, there are bugs and known issues. This build might not be mature enough for personal use. However, you can now use Beta and Stable builds side by side. Beta builds will have a purple icon instead of Wino blue accented icons.

• People and To Do mode requires additional scopes from Google side, which is still in verification. You may not be able to use those features with your Google accounts for now. If you are a serious user of those modes I can include you to the test group. Ping me on Discord.
• To Do mode designs are not completed. Expect visual issues and glitches with dark/light themes.
• Personalization -> Application Themes are premature. Specially custom theme creation page is nowhere near completed.
• People mode has some design and functionality issues and not very well tested yet. There are issues with contact pictures.
• IMAP tests are not completed yet. If you have an IMAP or CalDav server that was not working for you before, this build is a great one to test it with but it's not guaranteed to work.