diff --git a/scripts/release.js b/scripts/release.js
index e4d7fbe0..3dfe070e 100644
--- a/scripts/release.js
+++ b/scripts/release.js
@@ -120,6 +120,14 @@ const main = async () => {
     });
   }
 
+  // Copy the skills directory
+  const skillsDir = path.join(rootDir, 'skills');
+  if (fs.existsSync(skillsDir)) {
+    fs.cpSync(skillsDir, path.join(archiveDir, 'skills'), {
+      recursive: true,
+    });
+  }
+
   // Create the archive
   const output = fs.createWriteStream(path.join(releaseDir, archiveName));
   const archive = archiver('tar', {
diff --git a/skills/gmail/SKILL.md b/skills/gmail/SKILL.md
new file mode 100644
index 00000000..1024ce67
--- /dev/null
+++ b/skills/gmail/SKILL.md
@@ -0,0 +1,215 @@
+---
+name: gmail
+description: >
+  CRITICAL: You MUST activate this skill BEFORE composing, sending, drafting, or
+  searching emails. Always trigger this skill as the first step when the user
+  mentions "email", "gmail", or sending a message. Contains strict formatting
+  mandates that override default email behavior.
+---
+
+# Gmail Expert
+
+You are an expert at composing and managing email through the Gmail API. Follow
+these guidelines when helping users with email tasks.
+
+## Rich Text Email Formatting
+
+When composing emails (via `gmail.send` or `gmail.createDraft`), **always use
+HTML formatting with `isHtml: true`** unless the user explicitly requests plain
+text. Rich HTML emails look professional and are the standard for business
+communication.
+
+### Supported HTML Tags
+
+Gmail supports a broad set of HTML tags for email bodies. Use these freely:
+
+| Category | Tags                                                              |
+| :------- | :---------------------------------------------------------------- |
+| Text     | `<p>`, `<br>`, `<span>`, `<div>`, `<blockquote>`, `<pre>`, `<hr>` |
+| Headings | `<h1>` through `<h6>`                                             |
+| Emphasis | `<b>`, `<strong>`, `<i>`, `<em>`, `<u>`, `<s>`, `<strike>`        |
+| Code     | `<code>`, `<pre>`                                                 |
+| Lists    | `<ul>`, `<ol>`, `<li>`                                            |
+| Tables   | `<table>`, `<thead>`, `<tbody>`, `<tr>`, `<th>`, `<td>`           |
+| Links    | `<a href="...">`                                                  |
+| Images   | `<img src="..." alt="...">`                                       |
+
+### Inline CSS Styling
+
+Gmail strips `<style>` blocks and external stylesheets. **Always use inline
+CSS** via the `style` attribute:
+
+```html
+<!-- ✅ Correct: inline styles -->
+<p style="color: #333; font-family: Arial, sans-serif; font-size: 14px;">
+  Hello!
+</p>
+
+<!-- ❌ Wrong: style block (will be stripped) -->
+<style>
+  p {
+    color: #333;
+  }
+</style>
+```
+
+### Common Inline CSS Properties
+
+These CSS properties work reliably across Gmail clients:
+
+- **Typography**: `font-family`, `font-size`, `font-weight`, `font-style`,
+  `color`, `text-align`, `text-decoration`, `line-height`, `letter-spacing`
+- **Spacing**: `margin`, `padding` (use on `<td>` for table cell spacing)
+- **Borders**: `border`, `border-collapse` (on `<table>`)
+- **Background**: `background-color`
+- **Layout**: `width`, `max-width`, `height` (on tables and images)
+
+### Things to Avoid
+
+- ❌ `<script>` tags (blocked by all email clients)
+- ❌ `<style>` blocks (stripped by Gmail)
+- ❌ External stylesheets (`<link rel="stylesheet">`)
+- ❌ `position`, `float`, `flexbox`, `grid` (unreliable in email)
+- ❌ `background-image` on non-table elements (inconsistent support)
+- ❌ JavaScript event handlers (`onclick`, etc.)
+- ❌ Form elements (`<input>`, `<select>`, `<textarea>`)
+
+### Email Template Examples
+
+#### Professional Message
+
+```html
+<div style="font-family: Arial, sans-serif; font-size: 14px; color: #333;">
+  <p>Hi Team,</p>
+
+  <p>Please find the <b>Q4 results</b> summarized below:</p>
+
+  <table style="border-collapse: collapse; width: 100%; margin: 16px 0;">
+    <thead>
+      <tr style="background-color: #f2f2f2;">
+        <th style="border: 1px solid #ddd; padding: 8px; text-align: left;">
+          Metric
+        </th>
+        <th style="border: 1px solid #ddd; padding: 8px; text-align: left;">
+          Result
+        </th>
+      </tr>
+    </thead>
+    <tbody>
+      <tr>
+        <td style="border: 1px solid #ddd; padding: 8px;">Revenue</td>
+        <td style="border: 1px solid #ddd; padding: 8px;">$1.2M</td>
+      </tr>
+      <tr>
+        <td style="border: 1px solid #ddd; padding: 8px;">Growth</td>
+        <td style="border: 1px solid #ddd; padding: 8px;">+15%</td>
+      </tr>
+    </tbody>
+  </table>
+
+  <p>Key takeaways:</p>
+  <ul>
+    <li>Revenue exceeded targets by <b>12%</b></li>
+    <li>Customer retention improved to <b>94%</b></li>
+  </ul>
+
+  <p>
+    Best regards,<br />
+    <span style="color: #666;">— The Analytics Team</span>
+  </p>
+</div>
+```
+
+#### Styled Action Email
+
+```html
+<div
+  style="font-family: 'Helvetica Neue', Arial, sans-serif; max-width: 600px;"
+>
+  <h2 style="color: #1a73e8; margin-bottom: 8px;">Action Required</h2>
+  <p style="font-size: 14px; color: #555;">
+    Your review is needed on the following document:
+  </p>
+  <p>
+    <a
+      href="https://docs.google.com/document/d/example"
+      style="display: inline-block; background-color: #1a73e8; color: #fff;
+              padding: 10px 24px; text-decoration: none; border-radius: 4px;
+              font-size: 14px;"
+    >
+      Open Document
+    </a>
+  </p>
+  <p style="font-size: 12px; color: #999;">
+    Please respond by end of business Friday.
+  </p>
+</div>
+```
+
+## Gmail Search Syntax
+
+Use Gmail search operators with `gmail.search` for precise results:
+
+| Operator      | Example                    | Description                     |
+| :------------ | :------------------------- | :------------------------------ |
+| `from:`       | `from:alice@example.com`   | Sender                          |
+| `to:`         | `to:bob@example.com`       | Recipient                       |
+| `subject:`    | `subject:quarterly report` | Subject line                    |
+| `is:`         | `is:unread`, `is:starred`  | Message state                   |
+| `has:`        | `has:attachment`           | Has attachments                 |
+| `in:`         | `in:inbox`, `in:trash`     | Location                        |
+| `label:`      | `label:work`               | By label                        |
+| `before:`     | `before:2025/01/01`        | Before date                     |
+| `after:`      | `after:2025/01/01`         | After date                      |
+| `newer_than:` | `newer_than:7d`            | Within last N days/months/years |
+| `older_than:` | `older_than:1m`            | Older than N days/months/years  |
+| `filename:`   | `filename:report.pdf`      | Attachment filename             |
+| `size:`       | `size:5m`                  | Larger than size                |
+| `larger:`     | `larger:10M`               | Larger than size                |
+| `smaller:`    | `smaller:1M`               | Smaller than size               |
+| `OR`          | `from:alice OR from:bob`   | Either condition                |
+| `-`           | `-from:noreply@`           | Exclude                         |
+| `""`          | `"exact phrase"`           | Exact match                     |
+
+Combine operators for precise searches:
+`from:alice@example.com has:attachment newer_than:30d subject:report`
+
+## Label Management
+
+### System Labels
+
+System labels use their name directly as the ID. Use `gmail.modify` to apply
+these common operations:
+
+| Label       | Add Effect       | Remove Effect               |
+| :---------- | :--------------- | :-------------------------- |
+| `INBOX`     | Move to inbox    | Archive (remove from inbox) |
+| `UNREAD`    | Mark as unread   | Mark as read                |
+| `STARRED`   | Star the message | Unstar                      |
+| `IMPORTANT` | Mark important   | Mark not important          |
+| `SPAM`      | Mark as spam     | Remove spam classification  |
+| `TRASH`     | Move to trash    | Remove from trash           |
+
+### Custom Labels
+
+For user-created labels, you must resolve the label ID first:
+
+1. Call `gmail.listLabels()` to get all labels with their IDs
+2. Match the desired label by name
+3. Use the label ID (e.g., `Label_42`) in `gmail.modify`
+
+## Downloading Attachments
+
+1. Use `gmail.get` with `format: 'full'` to get attachment metadata (IDs and
+   filenames)
+2. Use `gmail.downloadAttachment` with the `messageId` and `attachmentId`
+3. **Always use absolute paths** for `localPath` (e.g.,
+   `/Users/username/Downloads/file.pdf`). Relative paths will be rejected.
+
+## Threading and Replies
+
+- Use `threadId` with `gmail.createDraft` to create a reply draft linked to an
+  existing conversation
+- The service automatically fetches reply headers (`In-Reply-To`, `References`)
+  from the thread to maintain proper threading
+- Always reference previous messages when replying for context continuity
diff --git a/workspace-server/WORKSPACE-Context.md b/workspace-server/WORKSPACE-Context.md
index cfe54c07..e6582a0f 100644
--- a/workspace-server/WORKSPACE-Context.md
+++ b/workspace-server/WORKSPACE-Context.md
@@ -89,21 +89,6 @@ When creating documents in specific folders:
 3. Create event with proper timezone handling
 4. Always show times in user's local timezone
 
-### Email Search and Response
-
-1. Search with `gmail.search()` using appropriate query syntax
-2. Get full content with `gmail.get()` if needed
-3. Preview any reply before sending
-4. Use threading context when responding
-
-### Adding/Removing Labels from Emails
-
-1. For system labels, including "INBOX", "SPAM", "TRASH", "UNREAD", "STARRED",
-   "IMPORTANT", the ID is the name itself.
-2. For user created custom labels, retrieve label ID with `gmail.listLabels()`.
-3. Use `gmail.modify()` to add or remove labels from emails with a single call
-   using label IDs.
-
 ### Event Deletion
 
 When using `calendar.deleteEvent`:
@@ -146,30 +131,6 @@ When asked about "next meeting" or "today's schedule":
 - Convert all times appropriately before display
 - Include timezone abbreviation (EST, PST, etc.) for clarity
 
-## 📧 Gmail & Chat Guidelines
-
-### Search Strategies
-
-- Use Gmail search syntax: `from:email@example.com is:unread`
-- Combine multiple criteria for precise results
-- Include SPAM/TRASH only when explicitly needed
-
-### Threading and Context
-
-- Maintain conversation context in replies
-- Reference previous messages when relevant
-- Use appropriate reply vs. new message based on context
-
-### Downloading Attachments
-
-1. **Find Attachment ID**: Use `gmail.get` with `format='full'` to retrieve
-   message details, including `attachments` metadata (IDs and filenames).
-2. **Download**: Use `gmail.downloadAttachment` with the specific `messageId`
-   and `attachmentId`.
-3. **Absolute Paths**: Always provide an **absolute path** for the `localPath`
-   argument (e.g., `/Users/username/Downloads/file.pdf`). Relative paths will be
-   rejected for security.
-
 ## 💬 Chat Guidelines
 
 Google Chat uses a specific subset of Markdown. Ensure messages sent to Chat use
@@ -309,9 +270,8 @@ Choose output format based on use case:
 
 ### Gmail
 
-- Full threading support
-- Label-based organization
-- Draft creation and management
+- See the **Gmail skill** for detailed guidance on composing rich HTML emails,
+  search syntax, label management, attachments, and threading.
 
 ### Google Chat