Context Awareness

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.

What it is

Context Awareness identifies the app you're using and adjusts your dictation accordingly. It improves accuracy by detecting names in emails, applies your Style Personalization settings based on the app category, and handles smart formatting in apps like Notion.

When to use it

Use this feature when you want to:

• Dictate emails and have Flow automatically recognize recipient names and apply a professional tone.

• Switch between apps like Slack and Google Docs without manually adjusting your writing style.

• Dictate into Notion without Flow picking up placeholder hint text.

How it works in Flow

Overview

Flow reads a limited amount of text near your cursor and identifies your active app. For browser-based apps, Flow identifies the specific website, so Gmail, Google Docs, and other web apps are recognized individually.

Flow recognizes four app categories: Email, Work messaging, Personal messaging, and Other.

Key behaviors

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

• Style matching: Flow detects your active app's category and applies the matching Style Personalization settings you configured during onboarding.

• Proper-noun preservation: Mid-sentence lowercasing is skipped when the dictated text starts with a proper noun that matches your first or last name, your personal dictionary, your team dictionary, or names visible on screen.

• Conversation context: Flow reads conversation context in Slack and Apple Messages for better transcription accuracy. Other apps benefit from general nearby-text reading but do not have dedicated conversation context support.

• Smart formatting in Notion and AI chat apps: In Notion, Flow skips context-aware formatting when the surrounding text is 2 words or fewer, or ends with "…", so dictation appears cleanly. In AI chat apps like Claude, Flow ignores placeholder hint text such as "Reply to Claude…" or "Tip: Hit ⌘J for AI".

• Browser recognition: Chrome, Safari, Arc, Brave, Edge, Firefox, Opera, Vivaldi, Zen Browser, Yandex Browser, Sidekick, and Shift are supported. Flow identifies the specific website rather than the browser. When a website cannot be identified quickly, Flow falls back to the browser name without specific-site recognition. Slack's Mac app is also URL-aware.

• Context-aware formatting: Flow adjusts casing, spacing, and punctuation based on surrounding text. When continuing mid-sentence, the first letter is lowercased and leading or trailing spaces are added as needed. Trailing periods are handled by writing style: Formal keeps them, Casual strips them for shorter dictations, and Very Casual always strips them. Trailing "!" and "?" are only removed for mid-sentence continuation or when text is selected. Stripping is skipped if the line already has punctuation.

• Persistent context in code editors: Flow remembers file names seen in Cursor, Windsurf, and VS Code across dictation sessions. File tagging and special formatting apply to Cursor and Windsurf only; VS Code is included for file-name memory only. File-name tagging in Cursor and Windsurf requires filenames to contain a ".", have no spaces, and start with a letter — so files like ".eslintrc" or names starting with digits are not tagged.

Privacy protections

• Context data handling: Context data is collected locally on your device and sent to Wispr as part of each dictation request, unless Privacy Mode is on. Context includes 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 list of apps in your current session, a screenshot, and conversation history (participant IDs and message roles/content).

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

• Privacy Mode: When enabled, no dictation or context data is retained or used for training. Privacy Mode is permanently locked on if you have signed the HIPAA Business Associate Agreement (BAA), or if your enterprise admin has enforced zero data retention or disabled data sharing for the organization.

• Accessibility permissions: On Mac, you must grant accessibility permissions in System Settings for Context Awareness to function. On Windows, no explicit accessibility permissions are required.

Examples

FAQs

Limitations and notes

• Context Awareness is available on Mac and Windows. On Windows, context-aware formatting is skipped when dictating inside the Wispr Flow app window itself. Otherwise the feature runs on both platforms.

• On Mac, accessibility permissions must be granted in System Settings for Context Awareness to function.

• On Enterprise plans, admins can disable Context Awareness for all users from the organization admin portal. When an admin disables it, the user toggle is forced off and locked.

• Enterprise organizations can enforce local data deletion policies (auto-delete after 24 hours, or never store) separately from zero data retention. Admins can also enforce a floor for local data storage, restricting or locking users to more aggressive settings.

• Local data storage options are available in Settings → Data and Privacy: Store data locally (default), Auto-delete local data every 24 hours (deletes transcripts, polish history, and instruct-mode history older than 24 hours), and Never store data locally (immediately deletes all transcripts, polish history, and instruct-mode history). Both deletion options show a confirmation dialog.

• Context reading has built-in performance safeguards so dictation is never slowed down. These safeguards apply across supported apps, including code editors like Cursor and VS Code.

• File tagging in Cursor and Windsurf does not run inside the IDE terminal, when a dictionary substitution was applied to the transcript, or when the IDE File Tagging setting is turned off. Only filenames with an extension (e.g., file.ts) are tagged, and filenames must contain a ".", have no spaces, and start with a letter.