Context Awareness

Last updated: October 9, 2026

Available on: Mac, Windows, iOS (limited to the focused text field)

Context Awareness reads your active app and adapts transcription accuracy, style, and formatting automatically, so emails sound like emails and Slack messages sound like Slack messages. It's on by default.

How it works in Flow

Flow reads text near your cursor and sorts your active app into one of four categories: Email, Work messaging, Personal messaging, and Other. In browsers, Flow identifies the website rather than the browser, so Slack in Chrome is Work messaging and Gmail in Chrome is Email. Google products (Gmail, Docs, Gemini, Calendar, Meet, Drive, Chat, AI Studio, and Colab) are recognized separately, and one service reached by different URLs or as a web app counts as one app. System processes and Wispr Flow itself are excluded.

Key behaviors

  • Improved accuracy: Flow uses names and context visible on screen, such as email recipients, to recognize proper nouns and preserve capitalization.

  • Context-aware formatting: Flow matches casing, spacing, and punctuation to surrounding text. Continuing mid-sentence lowercases the first letter and adds leading spaces, but lowercasing is skipped when your text starts with a proper noun matching your first or last name, your personal or team dictionary, or a name visible on screen. Trailing periods follow your writing style: Formal keeps them, Casual strips them for shorter dictations, Very Casual always strips them. Trailing "!" and "?" are removed only for mid-sentence continuation or when text is selected, and never when the line already has punctuation. On Mac and Windows, this matching happens on your device and also runs when Context Awareness is off.

  • Browser recognition: Chrome, Safari, Arc, Brave, Edge, Firefox, Opera, Vivaldi, Zen Browser, Yandex Browser, Sidekick, and Shift are supported. When a website cannot be identified quickly, Flow falls back to the browser name without specific-site recognition.

  • Empty boxes with placeholder text: On Windows, a text box showing only its own placeholder or label — such as the "Type a message" composer in Microsoft Teams and other Chromium-based editors — is treated as empty, so your first word is capitalized and no leading space is added. If you type text that exactly matches the box's label, that one dictation may not match spacing and casing; existing text is never deleted.

  • Missive: Missive counts as Email in the browser and in the Mac desktop app, so your chosen Email style and email formatting (greetings, sign-offs, line breaks) apply. The Missive desktop app on Windows is treated as Other.

  • Notion: Flow skips context-aware formatting when surrounding text is very short or looks like placeholder text.

  • Code editors: File tagging and special formatting apply to Cursor and Windsurf only.

Privacy protections

  • What context includes: When Context Awareness is on, context can accompany your dictation: app info, textbox contents (before, selected, and after the cursor), on-screen text, variable and file names in coding apps, your user identifier within the app, the apps in your current session, and conversation history (participant IDs and message roles and content). Context Awareness works from text and does not take screenshots. Captured text, extracted names, and counts for a dictation are cleared when that dictation ends.

  • iPhone: The keyboard sends the text before and after your cursor, and any selected text, with each dictation, along with the app name. There's no Context Awareness switch on iPhone.

  • Password fields excluded: Password field contents are never read or included in context; your audio is still transcribed as normal. Standard macOS password fields are excluded automatically, but custom or web-based password fields may be read like normal text fields.

  • Other exclusions: Flow excludes sensitive and numeric-only fields and browser URL bars, filters out placeholder and hint text, and skips context reading entirely in banking and financial apps and inside Wispr Flow.

  • Accessibility permissions: On Mac, grant accessibility permissions in System Settings for Context Awareness to work. Windows requires none.

  • Separate from other privacy settings: Turning off Improve the model for everyone (on by default for Free and Pro, off for Enterprise) does not turn off Context Awareness or Dictation Cloud Storage. Check each setting separately.

Note: For sensitive environments (legal, healthcare, or regulated data), turn Context Awareness off in Settings → Data and Privacy.

Examples

Dictating an email in Gmail

What happens: Flow reads the recipient's name and applies email-appropriate capitalization and punctuation.

You say: "hey alex thanks for sending over the proposal i'll review it by friday"

Flow types: Hey Alex, thanks for sending over the proposal. I'll review it by Friday.

Continuing a message in Slack

What happens: Flow matches the casing and punctuation of the text already in the message box.

You say: "sounds good let's sync tomorrow morning"

Flow types: sounds good, let's sync tomorrow morning

FAQs

How do I turn off Context Awareness?

Go to Settings → Data and Privacy and toggle off Context awareness. If your organization has disabled it for all users, the toggle is off and locked, with the tooltip "This setting is managed by your organization."

What is still sent when Context Awareness is off?

On Mac and Windows, Flow still sends the app name and website domain with each dictation, because it uses them to set the right tone. Flow still reads the text immediately around your cursor, but uses it only on your device to match capitalization, spacing, and punctuation; that text isn't sent, and no other on-screen text is read. Command Mode and Polish send the text you're editing so it can be changed.

Is Context Awareness HIPAA compliant?

It is compatible with HIPAA workflows: sign the applicable Business Associate Agreement (BAA), which locks Improve the model for everyone and Dictation Cloud Storage off, and disable Context Awareness separately if needed. Revoking a personal BAA in Settings → Data and Privacy removes that agreement's locks but not other organization restrictions, so review the implications first. Organization BAAs are managed by authorized administrators in the Admin Portal.

Can admins control Context Awareness organization-wide?

On Growth, each person controls their own setting and administrators cannot enforce it off. On Enterprise, admins choose Available, which lets each member control their own toggle but does not force it on, or Disable for all users, which turns it off for everyone on Mac and Windows and locks the setting.

Limitations and notes

  • On Windows, conversation context and element descriptions are Mac-only, and context-aware formatting is skipped inside the Wispr Flow app window.

  • Context reading is skipped for any dictation where it cannot complete quickly, so dictation is never slowed down.

  • File tagging in Cursor and Windsurf does not run inside the terminal, when a dictionary substitution was applied to the transcript, or when the IDE File Tagging setting is off. File names must include an extension (for example, file.ts), contain no spaces, and start with a letter, so ".eslintrc" or names starting with digits are not tagged.