Task Attachments and Files

Difficulty: Beginner

Overview

Many tasks require supporting files—design mockups, requirements documents, screenshots, data files, or reference materials. Instead of hunting through email attachments or shared drives, Waymaker lets you attach files directly to tasks, keeping everything organized in one place.

This guide teaches you how to upload files to tasks, preview and download attachments, manage multiple file versions, understand storage limits, organize files effectively, and apply best practices for file management in collaborative environments.

What You'll Learn

• How to upload files and images to tasks (drag-drop, file picker)
• Supported file types and size limits
• Previewing attachments without downloading
• Downloading and sharing attached files
• Managing multiple file versions
• Understanding board storage limits
• Organizing files across tasks
• Deleting and archiving attachments
• File attachment best practices

Prerequisites

• A Waymaker account with access to taskboards
• An existing taskboard with tasks (or create one following Creating Your First Taskboard)
• Understanding of basic task management (see Basic Task Management)
• At least Member permissions on the taskboard (to attach files)

Uploading Files to Tasks

Method 1: Drag-and-Drop Upload

Drag files directly onto a task:

1. Open the task (click any task card)
2. Locate the "Attachments" section in the task details modal
3. Drag one or more files from your desktop/file explorer
4. Drop them onto the attachments area (highlighted in blue when hovering)
5. Files upload automatically
6. Upload progress bar appears for each file
7. Files appear in the attachments list once upload completes

Drag-and-Drop Tips:

• You can drop multiple files at once (select multiple files before dragging)
• Drop zone appears when you drag a file over the task modal
• Large files show upload progress percentage

Method 2: File Picker Upload

Use the file picker button:

1. Open the task
2. Locate the "Attachments" section
3. Click the "Attach File" or "Upload" button
4. Your system file picker opens
5. Navigate to the file you want to upload
6. Select the file (or Ctrl+Click / Cmd+Click for multiple files)
7. Click "Open"
8. Files upload automatically

File Picker Tips:

• Hold Ctrl (Windows) or Cmd (Mac) to select multiple files
• Hold Shift to select a range of files
• Use search in file picker to find files quickly

Method 3: Paste Images from Clipboard

Paste screenshots or copied images directly:

1. Copy an image to your clipboard (screenshot tool, or copy image from browser)
2. Open the task
3. Click in the Attachments area or Description field
4. Press Ctrl+V (Windows) or Cmd+V (Mac)
5. Image uploads automatically
6. Image appears as an attachment with auto-generated name ("pasted-image-YYYYMMDD.png")

Paste Tips:

• Great for quickly adding screenshots
• Works for images copied from web pages
• Does not work for files (only images in clipboard)

Method 4: Upload from Comments

Attach files while commenting:

1. Open the task and scroll to the comments section
2. Click the "Attach file" icon in the comment toolbar
3. Select file from file picker or drag-and-drop onto comment box
4. File appears as attachment preview in comment
5. Post comment
6. File is attached to the task and linked in the comment

Comment Attachment Benefits:

• Provides context for the attachment ("Here's the updated mockup @sarah mentioned")
• File appears in both attachments list and comment thread
• Notifies mentioned users about the file

Supported File Types and Limits

Supported File Types

Waymaker supports most common file types. Here are the categories:

Documents:

• Microsoft Office: .docx, .xlsx, .pptx, .doc, .xls, .ppt
• PDFs: .pdf
• Text: .txt, .md, .csv, .rtf
• Google Docs links (saved as link, not uploaded file)

Images:

• Common formats: .jpg, .jpeg, .png, .gif, .svg, .webp
• Professional formats: .bmp, .tiff, .ico

Design Files:

• Figma links
• Sketch: .sketch
• Adobe: .psd, .ai, .indd (may not preview)

Compressed Archives:

• .zip, .rar, .7z, .tar, .gz

Code and Development:

• .js, .ts, .py, .java, .html, .css, .json, .xml, .sql
• .log, .env (be careful with sensitive data!)

Audio and Video:

• Audio: .mp3, .wav, .m4a, .flac
• Video: .mp4, .mov, .avi, .mkv, .webm

Other:

• .sketch, .fig (Figma), .xd (Adobe XD)
• .ics (calendar files)
• Almost any file type can be uploaded

File Size Limits

Per-File Limit:

• Maximum file size: 100 MB per file (may vary by plan)
• Files larger than 100 MB must be stored externally (Google Drive, Dropbox) and linked

Board Storage Limit:

• Free/Starter Plan: 2 GB per board
• Team Plan: 10 GB per board
• Enterprise Plan: 100 GB per board (or custom)

Checking Storage Usage:

1. Open Board Settings → "Storage" tab
2. View current usage: "Using 1.2 GB of 10 GB (12%)"
3. See list of largest files
4. Delete old files to free up space

What Happens When You Hit the Limit:

• Upload fails with error: "Board storage limit reached"
• You must delete old files or upgrade plan
• Admins receive email notification at 80% and 100% storage

Previewing Attachments

In-App File Preview

Supported Preview Types:

Images (full preview):

• Click any image attachment
• Opens full-size preview modal
• Navigation arrows to view other images
• Zoom controls (zoom in/out)
• Download button

PDFs (embedded preview):

• Click PDF attachment
• Opens in-app PDF viewer
• Scroll through pages
• Zoom and search text
• Download or print

Text Files (syntax-highlighted):

• .txt, .md, .json, .js, etc.
• Opens in-app code viewer with syntax highlighting
• Line numbers
• Copy code button

Videos (embedded player):

• .mp4, .webm, .mov
• In-app video player
• Play/pause, scrub timeline, volume control
• Download video

No Preview Available:

• Office files (.docx, .xlsx, .pptx): Download to open
• Design files (.sketch, .psd, .ai): Download to open in native app
• Compressed files (.zip, .rar): Download to extract

Preview Actions

While previewing:

• Download: Click download icon to save file locally
• Share Link: Copy direct link to file (permissions apply)
• Open in New Tab: Open preview in separate browser tab
• Delete: Remove attachment (if you have permission)
• Close Preview: Click X or press Escape

Downloading Attachments

Download Individual File

From Attachments List:

1. Open the task
2. Scroll to "Attachments" section
3. Hover over the file you want to download
4. Click the "Download" icon (download arrow)
5. File downloads to your browser's default download folder

From Preview Modal:

1. Click attachment to open preview
2. Click "Download" button in preview toolbar
3. File downloads immediately

Download Keyboard Shortcut:

• While hovering over a file: Ctrl+Shift+D (Windows) or Cmd+Shift+D (Mac)

Download All Attachments

Download all files as ZIP archive:

1. Open the task with multiple attachments
2. Click "Download All" button (above attachments list)
3. All files are packaged into a single .zip file
4. ZIP file downloads with name: [Task Name]-attachments.zip
5. Extract ZIP file on your computer to access individual files

Use Cases for Download All:

• Backing up task files
• Sharing complete set of files with external stakeholder
• Archiving completed task materials

Sharing File Links

Copy Direct Link:

1. Hover over attachment
2. Click "Copy Link" icon (link icon)
3. Link is copied to clipboard
4. Paste link in Slack, email, or browser

Link Permissions:

• Link only works for users with access to the board
• External users without board access get "Access Denied"
• Use guest access if you need to share files with externals

Managing File Versions

Uploading New Versions

Replacing a File with Updated Version:

Option 1: Upload with Same Name (Recommended)

1. Upload new file with the exact same filename
2. System detects duplicate name
3. Prompt: "A file with this name already exists. Replace or keep both?"
4. Select "Replace"
5. Old version is archived (see version history)
6. New version appears as the current file

Option 2: Manual Naming Convention

• Use version numbers: mockup-v1.png, mockup-v2.png, mockup-v3.png
• Use dates: mockup-2025-10-10.png, mockup-2025-10-11.png
• Both versions appear in attachments list
• Delete old versions manually when no longer needed

Version History (Future Feature)

Automatic Version Tracking:

• When you replace a file, Waymaker stores previous versions
• Click "Version History" next to filename
• View list of all versions with timestamps
• Restore previous version if needed
• Download any historical version

Check if Available:

• Look for "Version History" or "X versions" indicator next to filename
• If not available, use manual naming convention

Understanding Storage Management

Board Storage Quota

Viewing Storage Usage:

1. Open Board Settings (gear icon)
2. Navigate to "Storage" tab
3. View storage breakdown:
   • Total used: 5.2 GB of 10 GB (52%)
   • Files by type: Images: 3.1 GB, Documents: 1.8 GB, Other: 0.3 GB
   • Largest files: Top 10 files consuming most space

Storage by Task:

• See which tasks have the most attachments
• Identify tasks with large files to clean up

Freeing Up Storage Space

When approaching storage limit:

Step 1: Identify Large Files

• Board Settings → Storage → Sort by Size (descending)
• Look for files >10 MB

Step 2: Delete Unnecessary Files

• Old versions of files (if new version uploaded)
• Duplicate files
• Temporary files or test uploads
• Files for completed/archived tasks

Step 3: Move Large Files Externally

• Upload large files to Google Drive, Dropbox, or OneDrive
• Replace file attachment with a link in task description
• Example: Replace 80MB video file with YouTube or Drive link

Step 4: Archive Completed Tasks

• Completed tasks may still hold attachments
• Archive board (if supported) to move old data to cold storage
• Or export/delete old completed tasks

Storage Best Practices

✅ DO:

• Compress large images before uploading (use TinyPNG or similar)
• Use cloud storage links for very large files (>50 MB)
• Regularly clean up old or duplicate files
• Set up automated cleanup rules (if available)

❌ DON'T:

• Upload raw video files (use YouTube/Vimeo instead)
• Upload source code repositories (use Git links instead)
• Attach every possible file "just in case"
• Let storage reach 100% (plan cleanup at 80%)

Organizing Files Across Tasks

File Naming Conventions

Use Clear, Descriptive Filenames:

❌ Bad Filenames:

• Screenshot.png (too generic)
• File1.pdf (meaningless)
• Final_FINAL_v3_REAL.docx (messy)
• IMG_1234.jpg (camera default)

✅ Good Filenames:

• homepage-mockup-desktop-v2.png (descriptive + version)
• Q4-marketing-budget-approved.xlsx (context + status)
• user-interview-transcript-john-smith.pdf (type + subject)
• api-integration-diagram-2025-10-10.png (type + date)

Naming Convention Template:

[project]-[feature]-[type]-[version/date].[ext]

Examples:

• waymaker-auth-api-spec-v1.pdf
• homepage-hero-mockup-2025-10-10.png
• user-flow-checkout-final.pdf

Cross-Task File References

When the same file is needed on multiple tasks:

Option 1: Upload to Each Task (Duplicate)

• Pros: Each task is self-contained
• Cons: Uses more storage, versions can diverge

Option 2: Upload Once, Link to Original (Recommended)

1. Upload file to one "source of truth" task
2. In other tasks, add comment with link: "See mockups in task #123"
3. Or copy attachment link and paste in task description

Option 3: Use Board-Level Files (Future Feature)

• Some boards support board-level file storage
• Files available to all tasks without duplication
• Check if your board supports this

File Organization by Task Type

User Stories:

• Acceptance criteria document
• Mockups or wireframes
• User research data

Bugs:

• Screenshots showing the bug
• Error logs
• Video reproduction

Design Tasks:

• Design files (Figma links preferred)
• Asset exports (icons, images)
• Design specs

Development Tasks:

• Technical specs
• API documentation
• Code snippets (or links to PRs)

Deleting Attachments

Delete Single Attachment

Removing a file from a task:

1. Open the task
2. Scroll to "Attachments" section
3. Hover over the file you want to delete
4. Click the "Delete" icon (trash can)
5. Confirmation dialog: "Delete [filename]? This cannot be undone."
6. Click "Delete"
7. File is permanently removed

Who Can Delete Files:

• File uploader: Always (you can delete your own uploads)
• Task owner: Can delete any attachment on their task
• Board Admin/Owner: Can delete any attachment on any task
• Member/Viewer: Cannot delete others' uploads

Recovering Deleted Attachments

File Recovery:

• Deleted files are permanently removed (no trash/recycle bin currently)
• If you accidentally delete a file, you must re-upload it
• Future Feature: Trash bin with 30-day recovery period

Prevention:

• Double-check before clicking "Delete"
• Download important files as backup before deleting
• Use board storage export/backup if available

Troubleshooting

"Upload failed: File too large"

Possible causes:

• File exceeds 100 MB per-file limit
• Board storage quota is full

Solution:

1. Compress the file: Use ZIP compression or image compression tools
2. Split large files: Break into smaller parts (e.g., PDF pages)
3. Use external storage: Upload to Google Drive/Dropbox and link instead
4. Free up board storage: Delete old files to make space
5. Upgrade plan: If you regularly need large files, upgrade to a plan with higher limits

"File won't preview"

Possible causes:

• File type doesn't support in-app preview
• File is corrupted
• Browser issue

Solution:

1. Download and open locally: Many file types require native apps
2. Check file type: Office files, design files don't preview in-app
3. Try different browser: Some previews work better in Chrome vs Safari
4. Re-upload: If file is corrupted, re-upload from original source

"Can't find an attachment"

Possible causes:

• File is on a different task
• File was deleted
• You don't have permission to see the task

Solution:

1. Search for filename: Use board search to find tasks with that filename
2. Check activity timeline: See if file was deleted (shows in timeline)
3. Ask file uploader: They may remember which task it's on
4. Check related tasks: File might be on a parent/child task

Common Mistakes to Avoid

❌ Mistake 1: Uploading huge files that fill board storage

Problem: Uploading 50MB+ files without considering storage limits

Solution:

• Compress images before uploading (aim for <5 MB)
• Use YouTube/Vimeo for videos instead of uploading
• Use Google Drive/Dropbox links for large documents
• Regularly audit and clean up old files

❌ Mistake 2: Generic filenames

Problem: Files named "Screenshot.png", "Document.pdf", "File1.xlsx"

Solution: Use descriptive naming convention:

• Include project name, feature, version, date
• Example: homepage-hero-mockup-v2-2025-10-10.png
• Makes files searchable and understandable

❌ Mistake 3: Attaching sensitive data

Problem: Uploading files with passwords, API keys, personal data

Solution:

• Never attach .env files or credential files
• Redact sensitive information from screenshots
• Use password managers for credentials, not task attachments
• Check board permissions before uploading confidential data

❌ Mistake 4: Not cleaning up old files

Problem: Letting storage fill up with old versions and completed task files

Solution:

• Monthly cleanup: Delete files from completed tasks
• When uploading new version, delete old version
• Archive completed projects and remove attachments
• Set calendar reminder for quarterly file cleanup

Quick Reference

Upload File:

• Drag-drop onto task OR Click "Attach File" button → Select file

Preview File:

• Click attachment → Opens in-app preview (images, PDFs, videos, text)

Download File:

• Hover over attachment → Click download icon

Download All Files:

• Click "Download All" → Downloads ZIP of all attachments

Delete File:

• Hover over attachment → Click delete icon → Confirm

Check Storage:

• Board Settings → Storage tab → View usage

Supported Types:

• Documents (.pdf, .docx, .xlsx, .pptx, .txt, .md, .csv)
• Images (.jpg, .png, .gif, .svg, .webp)
• Videos (.mp4, .mov, .webm)
• Archives (.zip, .rar)
• Almost any file type (check size limit: 100 MB per file)

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Related Articles

• Basic Task Management - Task creation and lifecycle
• Rich Text Descriptions - Embed images in descriptions
• Task Comments and Activity Feed - Attach files to comments
• Board Settings & Configuration - Storage settings
• Guest Collaboration - Share files with external users

Next Steps

You now know how to attach and manage files on tasks! Ready to continue?

1. Bulk Task Operations - Edit multiple tasks at once
2. Task Checklists - Break tasks into sub-items
3. Creating & Managing Boards - Board setup and configuration

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Ready for next topic? → Bulk Task Operations