diff --git a/manifest.json b/manifest.json
index f28fa12..e78d160 100644
--- a/manifest.json
+++ b/manifest.json
@@ -1,6 +1,6 @@
 {
   "manifest_version": 3,
-  "version": "0.3.6",
+  "version": "0.4.0",
   "name": "Django Files",
   "description": "Django Files Web Extension designed to work with github.com/django-files/django-files.",
   "homepage_url": "https://github.com/django-files/web-extension",
diff --git a/src/css/main.css b/src/css/main.css
index 36b47d4..5cf9112 100644
--- a/src/css/main.css
+++ b/src/css/main.css
@@ -5,3 +5,7 @@ svg {
     width: 1em;
     margin-bottom: 0.15em;
 }
+
+#toast-container {
+    z-index: 4;
+}
diff --git a/src/css/options.css b/src/css/options.css
index f4ba43c..1b6159c 100644
--- a/src/css/options.css
+++ b/src/css/options.css
@@ -21,7 +21,7 @@ video {
 }
 
 .card {
-    min-width: 380px;
+    min-width: 400px;
 }
 
 .card,
diff --git a/src/css/popup.css b/src/css/popup.css
index 6ee0bd5..e105491 100644
--- a/src/css/popup.css
+++ b/src/css/popup.css
@@ -1,7 +1,7 @@
 /* CSS for popup.html */
 
 body {
-    width: 380px;
+    width: 400px;
     overflow-x: hidden;
 }
 
@@ -14,6 +14,7 @@ body {
     background-color: #303030;
 }
 
-#toast-container {
-    z-index: 4;
+ul.dropdown-menu {
+    max-width: 320px;
+    min-width: 180px;
 }
diff --git a/src/html/popup.html b/src/html/popup.html
index be817bb..d75d85e 100644
--- a/src/html/popup.html
+++ b/src/html/popup.html
@@ -24,10 +24,10 @@
 
 <div class="container-fluid p-2">
     <div class=" mb-1">
-        <div class="form-check form-switch float-start form-select-lg me-2" style="padding-top: 1px; padding-bottom: 0;"
+        <div class="form-check form-switch float-start form-select-lg me-2 pb-0" style="padding-top: 1px;"
              data-bs-title="Disable/Enable Mouseover Preview." data-bs-placement="bottom" data-bs-toggle="tooltip" data-bs-trigger="hover">
             <input class="form-check-input" id="popupPreview" type="checkbox" role="switch">
-            <label class="form-check-label visually-hidden" for="popupPreview" aria-describedby="popupPreviewHelp"></label>
+            <label class="form-check-label visually-hidden" for="popupPreview" aria-describedby="popupPreviewHelp">Popup Preview</label>
         </div>
         <a id="always-auth" class="d-none btn btn-sm btn-outline-warning float-start add-auth" role="button"
            data-bs-title="Update Authentication with Current Site." data-bs-placement="bottom" data-bs-toggle="tooltip" data-bs-trigger="hover">
@@ -57,42 +57,113 @@ <h3 class="my-0">Django Files</h3>
 
     <table id="files-table" class="d-none table table-striped table-hover table-sm small align-middle mb-0">
         <caption class="visually-hidden">Recent Uploads</caption>
-        <thead class="visually-hidden"><tr><th>Copy</th><th>File URL</th><th>Delete</th></tr></thead>
+        <thead class="visually-hidden"><tr><th>Menu</th><th>File URL</th></tr></thead>
         <tbody></tbody>
         <tfoot class="d-none">
         <tr>
             <td colspan="align-middle" style="width: 20px;"><i class="fa-solid fa-spinner fa-spin"></i></td>
             <td class="placeholder-glow"><span class="placeholder" style="width: 100%;"></span></td>
-            <td class="placeholder-glow" style="width: 20px;"><i class="fa-solid fa-circle-dot fa-xs"></i></td>
         </tr>
         </tfoot>
     </table>
 </div>
 
 <div aria-live="polite" aria-atomic="true" class="">
-    <div id="toast-container" class="toast-container bottom-0 end-0 p-3"></div>
+    <div id="toast-container" class="toast-container d-flex flex-column-reverse top-0 start-0 p-3"></div>
 </div>
 
 <div class="d-none">
-    <div class="toast align-items-center border-0 mt-3" role="alert" aria-live="assertive" aria-atomic="true" data-bs-delay="5000">
-        <div class="d-flex">
-            <div class="toast-body small"></div>
-            <button type="button" class="btn-close btn-close-white me-2 m-auto" data-bs-dismiss="toast" aria-label="Close"></button>
-        </div>
+    <div class="toast align-items-center border-0 mb-3" role="alert" aria-live="assertive" aria-atomic="true" data-bs-delay="5000">
+        <div class="toast-body text-break small"></div>
     </div>
-</div>
+
+    <input id="ctx-menu-row" type="hidden" value="">
+
+    <ul class="dropdown-menu py-1">
+        <li class="small"><a class="dropdown-item clip copy-link">
+            <i class="fa-solid fa-copy link-body-emphasis me-3"></i> Copy Share Link</a></li>
+        <li class="small"><a class="dropdown-item clip copy-raw">
+            <i class="fa-regular fa-copy link-body-emphasis me-3"></i> Copy Raw Link</a></li>
+        <li><hr class="dropdown-divider my-1"></li>
+        <li class="small"><a class="dropdown-item clip raw" href="">
+            <i class="fa-solid fa-arrow-up-right-from-square link-body-emphasis me-3"></i> Open Raw File</a></li>
+        <li class="small"><a class="dropdown-item" data-action="delete">
+            <i class="fa-regular fa-trash-can link-danger me-3"></i> Delete File</a></li>
+        <li><hr class="dropdown-divider my-1"></li>
+        <li class="dropdown-item-text text-center text-break small clip mouse-link py-0"></li>
+        <li class="dropdown-item-text text-center file-icons">
+            <span class="text-body-tertiary view-text">0</span>
+            <i class="fa-solid fa-eye text-body-tertiary mx-1"></i>
+            <a  data-action="private"><i class="fa-solid fa-lock mx-1 text-body-tertiary"></i></a>
+            <a class="pass-link" data-action="password"><i class="fa-solid fa-key mx-1 text-body-tertiary"></i></a>
+            <a class="text-decoration-none link-body-emphasis" data-action="expire">
+                <i class="fa-solid fa-hourglass-start mx-1 text-body-tertiary"></i>
+                <span class="expr-text"></span></a>
+        </li>
+    </ul>
+</div> <!-- d-none -->
 
 <div class="modal fade" id="delete-modal" tabindex="-1" aria-hidden="true">
 <div class="modal-dialog modal-dialog-centered">
 <div class="modal-content">
     <div class="modal-body text-center">
         <p>Are you sure you want to delete this file?</p>
-        <p><kbd id="delete-name" class="text-break"></kbd></p>
+        <p class="text-break"><kbd class="file-name"></kbd></p>
+    </div>
+    <div class="modal-footer">
+        <button type="button" class="btn btn-danger me-auto" id="confirm-delete">
+            <i class="fa-regular fa-trash-can me-2"></i> Delete</button>
+        <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">
+            Close <i class="fa-solid fa-xmark ms-2"></i></button>
+    </div>
+</div> <!-- modal-content -->
+</div> <!-- modal-dialog -->
+</div> <!-- modal -->
+
+<div class="modal fade" id="expire-modal" tabindex="-1" aria-hidden="true">
+<div class="modal-dialog modal-dialog-centered">
+<div class="modal-content">
+    <div class="modal-body">
+        <p class="text-center">
+            Set the file's expiration. <br>
+            For examples, see
+            <a href="https://github.com/onegreyonewhite/pytimeparse2#pytimeparse2-time-expression-parser" target="_blank" rel="noopener">
+                this README.md</a>.
+        </p>
+        <p class="text-center text-break"><kbd class="file-name"></kbd></p>
+        <form id="expire-form">
+            <label for="expire-input" class="form-label"><i class="fa-solid fa-hourglass-start me-1"></i> Expiration</label>
+            <input id="expire-input" aria-describedby="expire-input-help" class="form-control" type="text" autocomplete="off">
+            <div class="form-text" id="expire-input-help" >File Expiration (Blank to Disable Expiration).</div>
+        </form>
+    </div>
+    <div class="modal-footer">
+        <button type="submit" form="expire-form" class="btn btn-success me-auto">
+            <i class="fa-regular fa-floppy-disk me-2"></i> Save</button>
+        <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">
+            Close <i class="fa-solid fa-xmark ms-2"></i></button>
+    </div>
+</div> <!-- modal-content -->
+</div> <!-- modal-dialog -->
+</div> <!-- modal -->
+
+<div class="modal fade" id="password-modal" tabindex="-1" aria-hidden="true">
+<div class="modal-dialog modal-dialog-centered">
+<div class="modal-content">
+    <div class="modal-body">
+        <p class="text-center">Set the file's Password.</p>
+        <p class="text-center text-break"><kbd class="file-name"></kbd></p>
+        <form id="password-form">
+            <label for="password-input" class="form-label"><i class="fa-solid fa-key me-1"></i> Password</label>
+            <input id="password-input" aria-describedby="password-input-help" class="form-control" type="text" autocomplete="off">
+            <div class="form-text" id="password-input-help" >File Password (Blank to Disable Password).</div>
+        </form>
     </div>
     <div class="modal-footer">
-        <button type="button" class="btn btn-danger" id="confirm-delete">
-            Delete <i class="fa-regular fa-trash-can ms-1"></i></button>
-        <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">Close</button>
+        <button type="submit" form="password-form" class="btn btn-success me-auto">
+            <i class="fa-regular fa-floppy-disk me-2"></i> Save</button>
+        <button type="button" class="btn btn-secondary" data-bs-dismiss="modal">
+            Close <i class="fa-solid fa-xmark ms-2"></i></button>
     </div>
 </div> <!-- modal-content -->
 </div> <!-- modal-dialog -->
diff --git a/src/js/options.js b/src/js/options.js
index 3be260d..55865f2 100644
--- a/src/js/options.js
+++ b/src/js/options.js
@@ -17,12 +17,12 @@ document
  * @function initOptions
  */
 async function initOptions() {
-    // console.log('initOptions')
+    // console.debug('initOptions')
     document.getElementById('version').textContent =
         chrome.runtime.getManifest().version
 
     const { options } = await chrome.storage.sync.get(['options'])
-    console.log('options:', options)
+    console.debug('options:', options)
     updateOptions(options)
     if (!options?.siteUrl) {
         const siteUrl = document.getElementById('siteUrl')
@@ -42,10 +42,10 @@ async function initOptions() {
  * @param {String} namespace
  */
 function onChanged(changes, namespace) {
-    // console.log('onChanged:', changes, namespace)
+    // console.debug('onChanged:', changes, namespace)
     for (const [key, { newValue }] of Object.entries(changes)) {
         if (namespace === 'sync' && key === 'options') {
-            console.log('newValue:', newValue)
+            console.debug('newValue:', newValue)
             updateOptions(newValue)
         }
     }
@@ -57,7 +57,7 @@ function onChanged(changes, namespace) {
  * @param {FormDataEvent} event
  */
 async function saveOptions(event) {
-    // console.log('saveOptions:', event)
+    // console.debug('saveOptions:', event)
     const { options } = await chrome.storage.sync.get(['options'])
     if (event.target.type === 'checkbox') {
         options[event.target.id] = event.target.checked
@@ -75,8 +75,8 @@ async function saveOptions(event) {
     } else {
         options[event.target.id] = event.target.value
     }
-    console.log(`Set: "${event.target.id}" to target:`, event.target)
-    console.log('options:', options)
+    console.info(`Set: "${event.target.id}" to target:`, event.target)
+    console.debug('options:', options)
     await chrome.storage.sync.set({ options })
 }
 
@@ -87,7 +87,7 @@ async function saveOptions(event) {
  */
 function updateOptions(options) {
     for (const [key, value] of Object.entries(options)) {
-        // console.log(`${key}: ${value}`)
+        // console.debug(`${key}: ${value}`)
         const element = document.getElementById(key)
         if (element) {
             if (typeof value === 'boolean') {
diff --git a/src/js/popup.js b/src/js/popup.js
index 10c01dd..8afba5c 100644
--- a/src/js/popup.js
+++ b/src/js/popup.js
@@ -2,6 +2,11 @@
 
 chrome.runtime.onMessage.addListener(onMessage)
 document.addEventListener('DOMContentLoaded', initPopup)
+document.getElementById('expire-form').addEventListener('submit', expireForm)
+
+document
+    .getElementById('password-form')
+    .addEventListener('submit', passwordForm)
 document
     .getElementById('confirm-delete')
     .addEventListener('click', deleteConfirm)
@@ -18,6 +23,14 @@ document
     .querySelectorAll('[data-bs-toggle="tooltip"]')
     .forEach((el) => new bootstrap.Tooltip(el))
 
+document.querySelectorAll('.modal').forEach((el) =>
+    el.addEventListener('shown.bs.modal', (event) => {
+        const input = event.target.querySelector('input')
+        input?.focus()
+        input?.select()
+    })
+)
+
 const filesTable = document.getElementById('files-table')
 const errorAlert = document.getElementById('error-alert')
 const authButton = document.getElementById('auth-button')
@@ -25,13 +38,22 @@ const alwaysAuth = document.getElementById('always-auth')
 const mediaOuter = document.getElementById('media-outer')
 const mediaImage = document.getElementById('media-image')
 const mediaError = document.getElementById('media-error')
-const deleteName = document.getElementById('delete-name')
+const ctxMenuRow = document.getElementById('ctx-menu-row')
+const expireInput = document.getElementById('expire-input')
+const passwordInput = document.getElementById('password-input')
 const deleteModal = bootstrap.Modal.getOrCreateInstance('#delete-modal')
+const expireModal = bootstrap.Modal.getOrCreateInstance('#expire-modal')
+const passwordModal = bootstrap.Modal.getOrCreateInstance('#password-modal')
+
+const clipboard = new ClipboardJS('.clip')
+clipboard.on('success', () => showToast('Copied to Clipboard'))
+clipboard.on('error', () => showToast('Clipboard Copy Failed', 'warning'))
 
 const loadingImage = '../media/loading.gif'
 let authError = false
 let timeoutID
 let timeout
+let fileData
 
 /**
  * Initialize Popup
@@ -39,11 +61,11 @@ let timeout
  * @function initPopup
  */
 async function initPopup() {
-    console.log('initPopup')
+    console.debug('initPopup')
 
     // Get options
     const { options } = await chrome.storage.sync.get(['options'])
-    console.log('options:', options)
+    console.debug('options:', options)
 
     // Set Options (this is currently the only one in the popup)
     document.getElementById('popupPreview').checked = options.popupPreview
@@ -87,12 +109,11 @@ async function initPopup() {
         cache: 'no-cache',
     }
     let response
-    let data
     try {
         const url = new URL(`${options.siteUrl}/api/recent/`)
         url.searchParams.append('amount', options.recentFiles || '10')
         response = await fetch(url, opts)
-        data = await response.json()
+        fileData = await response.json()
     } catch (e) {
         console.warn(e)
         return displayAlert({
@@ -101,31 +122,41 @@ async function initPopup() {
             auth: true,
         })
     }
-    console.log(`response.status: ${response.status}`, response, data)
+    console.debug(`response.status: ${response.status}`, response, fileData)
 
     // Check response data is valid and has files
     if (!response?.ok) {
-        console.warn(`error: ${data.error}`)
-        return displayAlert({ message: data.error, type: 'danger', auth: true })
-    } else if (data === undefined) {
+        console.warn(`error: ${fileData.error}`)
+        return displayAlert({
+            message: fileData.error,
+            type: 'danger',
+            auth: true,
+        })
+    } else if (fileData === undefined) {
         return displayAlert({ message: 'Response Data Undefined.', auth: true })
-    } else if (!data.length) {
+    } else if (!fileData.length) {
         return displayAlert({ message: 'No Files Returned.' })
     }
 
     // Update table should only be called here, changes should use initPopup()
-    updateTable(data)
+    updateTable(fileData, options)
 
-    // Re-init clipboardJS and popupLinks after updateTable
-    new ClipboardJS('.clip')
+    // CTX menus are re-generated, eventListener re-addd
+    document
+        .querySelectorAll('[data-action]')
+        .forEach((el) => el.addEventListener('click', ctxMenu))
+
+    // File Links are re-generated, eventListener re-addd
     document
         .querySelectorAll('a[href]')
         .forEach((el) => el.addEventListener('click', popupLinks))
 
+    // Re-init clipboardJS after updateTable
+    new ClipboardJS('.clip')
+
     // Enable Popup Mouseover Preview if popupPreview
     timeout = options.popupTimeout * 1000
     if (options.popupPreview) {
-        console.log('Enabling Mouseover Preview')
         initPopupMouseover()
     }
 }
@@ -137,7 +168,7 @@ async function initPopup() {
  * @param {MouseEvent} event
  */
 async function popupLinks(event) {
-    console.log('popupLinks:', event)
+    console.debug('popupLinks:', event)
     event.preventDefault()
     const anchor = event.target.closest('a')
     console.log(`anchor.href: ${anchor.href}`)
@@ -157,8 +188,8 @@ async function popupLinks(event) {
 async function onMessage(message) {
     // console.log('onMessage: message, sender:', message, sender)
     if (message?.siteUrl && message?.authToken) {
-        console.log(`url: ${message.siteUrl}`)
-        console.log(`token: ${message.authToken}`)
+        console.debug(`url: ${message.siteUrl}`)
+        console.debug(`token: ${message.authToken}`)
         const { options } = await chrome.storage.sync.get(['options'])
         if (
             options?.siteUrl !== message.siteUrl ||
@@ -169,7 +200,7 @@ async function onMessage(message) {
                 authToken: message.authToken,
             }
             await chrome.storage.local.set({ auth })
-            console.log('New Authentication Found.')
+            console.info('New Authentication Found.')
             if (options.checkAuth) {
                 alwaysAuth.classList.remove('d-none')
             }
@@ -189,15 +220,15 @@ async function saveOptions(event) {
     // console.log('saveOptions:', event)
     const { options } = await chrome.storage.sync.get(['options'])
     options[event.target.id] = event.target.checked
-    console.log(`Set: "${event.target.id}" to target:`, event.target)
-    console.log('options:', options)
+    console.info(`Set: "${event.target.id}" to target:`, event.target)
+    console.debug('options:', options)
     await chrome.storage.sync.set({ options })
     if (event.target.id === 'popupPreview') {
         if (event.target.checked) {
-            console.log('popupPreview Enabled. Running initPopupMouseover...')
+            console.debug('popupPreview Enabled. Running initPopupMouseover...')
             initPopupMouseover()
         } else {
-            console.log('popupPreview Disabled. Removing Event Listeners...')
+            console.debug('popupPreview Disabled. Removing Event Listeners...')
             document.querySelectorAll('.link-underline').forEach((el) => {
                 el.removeEventListener('mouseover', onMouseOver)
                 el.removeEventListener('mouseout', onMouseOut)
@@ -213,15 +244,15 @@ async function saveOptions(event) {
  * @param {MouseEvent} event
  */
 async function authCredentials(event) {
-    console.log('authCredentials:', event)
+    console.debug('authCredentials:', event)
     const { auth } = await chrome.storage.local.get(['auth'])
-    console.log('auth:', auth)
+    console.debug('auth:', auth)
     if (auth?.authToken && auth?.siteUrl) {
         const { options } = await chrome.storage.sync.get(['options'])
         options.authToken = auth.authToken
         options.siteUrl = auth.siteUrl
         await chrome.storage.sync.set({ options })
-        console.log('Auth Credentials Updated...')
+        console.info('Auth Credentials Updated...')
         authButton.classList.add('d-none')
         errorAlert.classList.add('d-none')
         alwaysAuth.classList.add('d-none')
@@ -238,7 +269,7 @@ async function authCredentials(event) {
  * @param {Number} rows
  */
 function genLoadingData(rows) {
-    console.log('genLoadingData:', rows)
+    console.debug('genLoadingData:', rows)
     const number = parseInt(rows, 10)
     if (number > 0) {
         filesTable.classList.remove('d-none')
@@ -262,105 +293,298 @@ function genLoadingData(rows) {
  * Update Popup Table with Data
  * @function updateTable
  * @param {Array} data
+ * @param {Object} options
  */
-function updateTable(data) {
-    console.log('updateTable:', data)
+function updateTable(data, options) {
+    console.debug('updateTable:', data)
     const tbody = filesTable.querySelector('tbody')
     const length = tbody.rows.length
-    // console.log(`data.length: ${data.length}`)
-    // console.log(`tbody.rows.length: ${tbody.rows.length}`)
+    // console.debug(`data.length: ${data.length}`)
+    // console.debug(`tbody.rows.length: ${tbody.rows.length}`)
     for (let i = 0; i < length; i++) {
-        // console.log(`i: ${i}`)
+        // console.debug(`i: ${i}`)
         let row = tbody.rows[i]
         if (!row) {
             row = tbody.insertRow()
         }
         if (data.length === i) {
-            console.log('End of data. Removing remaining rows...')
+            console.info('End of data. Removing remaining rows...')
             const rowsToRemove = length - i
             for (let j = 0; j < rowsToRemove; j++) {
                 tbody.deleteRow(tbody.rows.length - 1)
             }
             break
         }
-        const value = data[i]
-        // TODO: This should not happen because of above condition
-        if (!value) {
-            console.warn(`No Data Value at Index: ${i}`, row)
-            continue
+        row.id = `row-${i}`
+        // TODO: Backwards Compatible with Older DJ Versions
+        let url
+        let name
+        let href
+        if (typeof data[i] === 'object') {
+            url = new URL(data[i].url)
+            name = data[i].name
+            href = data[i].url
+        } else {
+            url = new URL(data[i])
+            name = url.pathname.replace(/^\/u\//, '')
+            href = data[i]
         }
-        // TODO: This throws an error if value is not valid URL
-        const url = new URL(value)
-        const name = url.pathname.replace(/^\/u\//, '')
-
-        const copy = document.createElement('a')
-        copy.title = 'Copy'
-        copy.setAttribute('role', 'button')
-        copy.classList.add('link-body-emphasis', 'clip')
-        copy.innerHTML = '<i class="fa-regular fa-clipboard"></i>'
-        copy.dataset.clipboardText = value
-        copy.addEventListener('click', clipClick)
+        const raw = url.origin + url.pathname.replace(/^\/u\//, '/raw/')
+        let rawURL = new URL(raw)
+        const password = url.searchParams.get('password')
+        if (password) {
+            rawURL.searchParams.append('password', password)
+        }
+
+        // CTX Button -> 0
+        const button = document.createElement('a')
+        button.classList.add('link-body-emphasis', 'ctx-button')
+        button.setAttribute('role', 'button')
+        button.setAttribute('aria-expanded', 'false')
+        button.dataset.bsToggle = 'dropdown'
+        button.innerHTML = '<i class="fa-solid fa-bars"></i>'
+
+        // CTX Drop Down -> Menu
+        const drop = document
+            .querySelector('.d-none .dropdown-menu')
+            .cloneNode(true)
+        drop.id = `ctx-${i}`
+        if (typeof data[i] === 'object') {
+            updateContextMenu(drop, data[i]).then()
+        }
+        const fileName = drop.querySelector('li.mouse-link')
+        fileName.innerText = name
+        fileName.dataset.clipboardText = name
+        fileName.dataset.raw = `${raw}?token=${options.authToken}&view=gallery`
+        drop.querySelector('.copy-link').dataset.clipboardText = href
+        drop.querySelector('.copy-raw').dataset.clipboardText = rawURL.href
+        drop.querySelectorAll('.raw').forEach((el) => (el.href = rawURL.href))
+        button.appendChild(drop)
+
+        // Cell: 0
         const cell0 = row.cells[0]
         cell0.classList.add('align-middle')
         cell0.style.width = '20px'
         cell0.innerHTML = ''
-        cell0.appendChild(copy)
+        cell0.appendChild(button)
 
+        // File Link -> 1
         const link = document.createElement('a')
         link.text = name
         link.title = name
-        link.href = value
+        link.href = href
         link.setAttribute('role', 'button')
         link.classList.add(
             'link-underline',
             'link-underline-opacity-0',
             'link-underline-opacity-75-hover',
-            'file-link'
+            'file-link',
+            'mouse-link'
         )
         link.target = '_blank'
         link.dataset.name = name
-        link.dataset.raw =
-            url.origin +
-            url.pathname.replace(/^\/u\//, '/raw/') +
-            '?view=gallery'
+        link.dataset.row = i.toString()
+        link.dataset.raw = `${raw}?token=${options.authToken}&view=gallery`
+
+        // Cell: 1
         const cell1 = row.cells[1]
         cell1.classList.add('text-break')
         cell1.innerHTML = ''
         cell1.appendChild(link)
+    }
+}
 
-        const del = document.createElement('a')
-        del.title = 'Delete'
-        del.setAttribute('role', 'button')
-        del.classList.add('link-danger')
-        del.innerHTML = '<i class="fa-regular fa-trash-can"></i>'
-        del.addEventListener('click', deleteClick)
-        const cell2 = row.cells[2]
-        cell2.classList.add('align-middle')
-        cell2.style.width = '20px'
-        cell2.innerHTML = ''
-        cell2.appendChild(del)
+/**
+ * @function updateContextMenu
+ * @param {HTMLElement} ctx
+ * @param {Object} data
+ * @return {Promise<void>}
+ */
+async function updateContextMenu(ctx, data) {
+    // console.debug('updateContextMenu:', ctx, data)
+    if (data.view) {
+        const views = ctx.querySelector('.view-text')
+        views.innerText = data.view
+        enableEl(ctx, '.view-text')
+        enableEl(ctx, '.fa-eye')
+    }
+    if (data.private) {
+        enableEl(ctx, '.fa-lock', 'text-danger-emphasis')
+    }
+    if (data.password) {
+        enableEl(ctx, '.fa-key', 'text-warning-emphasis')
+        // const link = ctx.querySelector('.pass-link')
+        // link.classList.add('clip')
+        // link.dataset.clipboardText = data.password
+    } else {
+        disableEl(ctx, '.fa-key', 'text-warning-emphasis')
+    }
+    if (data.expr) {
+        enableEl(ctx, '.fa-hourglass-start')
+        ctx.querySelector('.expr-text').innerText = data.expr
+    } else {
+        disableEl(ctx, '.fa-hourglass-start')
+        ctx.querySelector('.expr-text').innerText = ''
     }
 }
 
+function enableEl(ctx, selector, add = 'text-body-emphasis') {
+    const el = ctx.querySelector(selector)
+    el.classList.remove('text-body-tertiary')
+    el.classList.add(add)
+}
+
+function disableEl(ctx, selector, remove = 'text-body-emphasis') {
+    const el = ctx.querySelector(selector)
+    el.classList.remove(remove)
+    el.classList.add('text-body-tertiary')
+}
+
 /**
- * Delete Click Callback
- * @function deleteClick
+ * Context Menu Click Callback
+ * @function ctxMenu
  * @param {MouseEvent} event
  */
-async function deleteClick(event) {
-    console.log('deleteClick:', event)
-    const closest = event.target?.closest('tr')?.querySelector('.file-link')
-    const name = closest.dataset?.name
-    console.log('name:', name)
-    if (!name) {
-        return console.error('No name for: event, closest', event, closest)
-    }
-    deleteName.textContent = name
-    const { options } = await chrome.storage.sync.get(['options'])
-    if (options.deleteConfirm) {
-        deleteModal.show()
+async function ctxMenu(event) {
+    console.debug('ctxMenu:', event)
+    event.preventDefault()
+    const anchor = event.target.closest('a')
+    // console.debug('anchor:', anchor)
+    const action = anchor.dataset?.action
+    console.debug('action:', action)
+    const fileLink = event.target?.closest('tr')?.querySelector('.file-link')
+    console.debug('row:', fileLink.dataset?.row)
+    if (!fileLink.dataset?.row) {
+        console.error('404: fileLink.dataset?.row - Fatal Error!')
+    }
+    ctxMenuRow.value = fileLink.dataset?.row
+    const file = fileData[fileLink.dataset?.row]
+    console.debug('file:', file)
+    let name
+    if (typeof file === 'object') {
+        name = file.name
     } else {
-        await deleteConfirm(event)
+        name = fileLink.dataset.name
+    }
+    console.debug('name:', name)
+    if (action === 'delete') {
+        document.querySelector('#delete-modal .file-name').textContent = name
+        const { options } = await chrome.storage.sync.get(['options'])
+        if (options.deleteConfirm) {
+            deleteModal.show()
+        } else {
+            await deleteConfirm(event)
+        }
+    } else if (action === 'expire') {
+        expireInput.value = file.expr
+        document.querySelector('#expire-modal .file-name').textContent = name
+        expireModal.show()
+    } else if (action === 'password') {
+        passwordInput.value = file.password
+        document.querySelector('#password-modal .file-name').textContent = name
+        passwordModal.show()
+    } else if (action === 'private') {
+        await togglePrivate()
+    }
+}
+
+async function togglePrivate() {
+    console.debug('togglePrivate')
+    // event.preventDefault()
+    const file = fileData[ctxMenuRow.value]
+    console.debug('file:', file)
+    const data = { private: !file.private }
+    const response = await handleFile(file.name, 'POST', data)
+    console.debug('response:', response)
+    if (response.ok) {
+        const json = await response.json()
+        console.debug('json:', json)
+        fileData[ctxMenuRow.value] = json
+        const ctx = document.getElementById(`ctx-${ctxMenuRow.value}`)
+        console.debug('ctx:', ctx)
+        if (json.private) {
+            enableEl(ctx, '.fa-lock', 'text-danger-emphasis')
+        } else {
+            disableEl(ctx, '.fa-lock', 'text-danger-emphasis')
+        }
+        showToast(`Privacy Updated: <b>${file.name}</b>`)
+    } else {
+        console.info(`Private Error: "${file.name}", response:`, response)
+        showToast(`Error Setting Privacy: <b>${file.name}</b>`, 'danger')
+    }
+}
+
+/**
+ * Password Form Submit Callback
+ * @function passwordForm
+ * @param {SubmitEvent} event
+ */
+async function passwordForm(event) {
+    console.debug('passwordForm:', event)
+    event.preventDefault()
+    const file = fileData[ctxMenuRow.value]
+    console.debug('file:', file)
+    const password = passwordInput.value
+    if (password === file.password) {
+        console.info(`Passwords Identical: ${password} === ${file.password}`)
+        showToast(`Passwords Identical: <b>${file.name}</b>`, 'warning')
+        return passwordModal.hide()
+    }
+    console.log(`Setting Password: "${password}" on file: ${file.name}`)
+    const data = { password: password }
+    // TODO: Catch Error? Throw should happen during init...
+    const response = await handleFile(file.name, 'POST', data)
+    console.debug('response:', response)
+    if (response.ok) {
+        showToast(`Password Updated: <b>${file.name}</b>`)
+        const json = await response.json()
+        console.debug('json:', json)
+        const ctx = document.getElementById(`ctx-${ctxMenuRow.value}`)
+        console.debug('ctx:', ctx)
+        fileData[ctxMenuRow.value] = json
+        await updateContextMenu(ctx, json)
+        passwordModal.hide()
+    } else {
+        console.info(`Password Error: "${password}", response:`, response)
+        showToast(`Error Setting Password: <b>${file.name}</b>`, 'danger')
+        passwordModal.hide()
+    }
+}
+
+/**
+ * Expire Form Submit Callback
+ * @function expireForm
+ * @param {SubmitEvent} event
+ */
+async function expireForm(event) {
+    console.debug('expireForm:', event)
+    event.preventDefault()
+    const file = fileData[ctxMenuRow.value]
+    console.debug('file:', file)
+    const expr = expireInput.value
+    if (expr === file.expr) {
+        console.info(`New Expire Value Same as Old: ${expr}`)
+        showToast(`New Expire same as Previous: <b>${file.name}</b>`, 'warning')
+        return expireModal.hide()
+    }
+    console.log(`Setting Expire: "${expr}" on file: ${file.name}`)
+    const data = { expr: expr }
+    // TODO: Catch Error? Throw should happen during init...
+    const response = await handleFile(file.name, 'POST', data)
+    console.debug('response:', response)
+    if (response.ok) {
+        showToast(`Expire Updated: <b>${file.name}</b>`)
+        const json = await response.json()
+        console.debug('json:', json)
+        const ctx = document.getElementById(`ctx-${ctxMenuRow.value}`)
+        console.debug('ctx:', ctx)
+        fileData[ctxMenuRow.value] = json
+        await updateContextMenu(ctx, json)
+        expireModal.hide()
+    } else {
+        console.info(`Error Setting Expire: "${expr}", response:`, response)
+        showToast(`Error Setting Expire: <b>${file.name}</b>`, 'danger')
+        expireModal.hide()
     }
 }
 
@@ -370,39 +594,49 @@ async function deleteClick(event) {
  * @param {MouseEvent} event
  */
 async function deleteConfirm(event) {
-    console.log('deleteConfirm:', event)
-    const name = deleteName.textContent
-    console.log(`Deleting File: ${name}`)
+    console.debug('deleteConfirm:', event)
+    event.preventDefault()
+    const file = fileData[ctxMenuRow.value]
+    console.debug('file:', file)
+    const name = document.querySelector('#delete-modal .file-name').textContent
+    console.log(`deleteConfirm await deleteFile: ${name}`)
     // TODO: Catch Error? Throw should happen during init...
-    const response = await deleteFile(name)
-    console.log('response:', response)
+    const response = await handleFile(name, 'DELETE')
+    console.debug('response:', response)
     if (response.ok) {
         mediaOuter.classList.add('d-none')
         deleteModal.hide()
         await initPopup()
     } else {
-        console.error(`Error Deleting File: "${name}", response:`, response)
-        showToast(`Error Deleting: <strong>${name}</strong>`, 'danger')
+        console.info(`Error Deleting: "${name}", response:`, response)
+        showToast(`Error Deleting: <b>${name}</b>`, 'danger')
         deleteModal.hide()
     }
 }
 
 /**
- * Post URL to endpoint
- * @function deleteFile
+ * Delete File Request
+ * @function handleFile
  * @param {String} name
+ * @param {String} method
+ * @param {Object} data
  * @return {Response}
  */
-async function deleteFile(name) {
-    console.log(`deleteFile: ${name}`)
+async function handleFile(name, method, data = null) {
+    console.debug(`handleFile: ${name}`)
     const { options } = await chrome.storage.sync.get(['options'])
-    // console.log('options:', options)
+    // console.debug('options:', options)
     const headers = { Authorization: options.authToken }
     const opts = {
-        method: 'DELETE',
+        method: method,
         headers: headers,
     }
-    const apiUrl = `${options.siteUrl}/api/delete/${name}`
+    if (data) {
+        opts.body = JSON.stringify(data)
+    }
+    // TODO: Update to /file/ Endpoint...
+    const apiUrl = `${options.siteUrl}/api/file/${name}`
+    // const apiUrl = `${options.siteUrl}/api/delete/${name}`
     return await fetch(apiUrl, opts)
 }
 
@@ -413,34 +647,20 @@ async function deleteFile(name) {
  * @param {String} type
  */
 function showToast(message, type = 'success') {
-    console.log(`showToast: ${type}:`, message)
-    const element = document.querySelector('.d-none .toast').cloneNode(true)
-    element.classList.add(`text-bg-${type}`)
-    element.querySelector('.toast-body').innerHTML = message
-    document.getElementById('toast-container').appendChild(element)
-    const toast = new bootstrap.Toast(element)
-    toast.show()
-    const callback = () => {
+    console.debug(`showToast: ${type}: ${message}`)
+    const clone = document.querySelector('.d-none .toast')
+    const container = document.getElementById('toast-container')
+    if (clone && container) {
+        const element = clone.cloneNode(true)
+        element.querySelector('.toast-body').innerHTML = message
+        element.classList.add(`text-bg-${type}`)
+        container.appendChild(element)
+        const toast = new bootstrap.Toast(element)
         element.addEventListener('mouseover', () => toast.hide())
+        toast.show()
+    } else {
+        console.info('Missing clone or container:', clone, container)
     }
-    setTimeout(callback, 1000)
-}
-
-/**
- * Clipboard Click Callback
- * @function clipClick
- * @param {MouseEvent} event
- */
-function clipClick(event) {
-    console.log('clipClick:', event)
-    const element = event.target.closest('a')
-    // console.log('element:', element)
-    element.classList.add('link-success')
-    element.classList.remove('link-body-emphasis')
-    setTimeout(() => {
-        element.classList.add('link-body-emphasis')
-        element.classList.remove('link-success')
-    }, 500)
 }
 
 /**
@@ -451,7 +671,7 @@ function clipClick(event) {
  * @param {Boolean} auth
  */
 function displayAlert({ message, type = 'warning', auth = false } = {}) {
-    console.log(`displayAlert: ${type}:`, message)
+    console.info(`displayAlert: ${type}:`, message)
     filesTable.classList.add('d-none')
     errorAlert.innerHTML = message
     errorAlert.classList.add(`alert-${type}`)
@@ -463,12 +683,13 @@ function displayAlert({ message, type = 'warning', auth = false } = {}) {
 }
 
 async function checkSiteAuth() {
+    console.debug('checkSiteAuth')
     try {
         const [tab] = await chrome.tabs.query({
             currentWindow: true,
             active: true,
         })
-        console.log('tab:', tab)
+        console.debug('tab:', tab)
         await chrome.scripting.executeScript({
             target: { tabId: tab.id },
             files: ['/js/auth.js'],
@@ -477,7 +698,7 @@ async function checkSiteAuth() {
 }
 
 function initPopupMouseover() {
-    console.log('initPopupMouseover')
+    console.debug('initPopupMouseover')
     mediaOuter.addEventListener('mouseover', () => {
         mediaOuter.classList.add('d-none')
         mediaImage.src = loadingImage
@@ -485,20 +706,20 @@ function initPopupMouseover() {
             clearTimeout(timeoutID)
         }
     })
-    mediaImage.addEventListener('error', () => {
-        // console.log('mediaError:', event)
+    mediaImage.addEventListener('error', (event) => {
+        console.debug('mediaError:', event)
         mediaImage.classList.add('d-none')
         mediaError.classList.remove('d-none')
         mediaImage.src = '../media/loading.gif'
     })
-    document.querySelectorAll('.file-link').forEach((el) => {
+    document.querySelectorAll('.mouse-link').forEach((el) => {
         el.addEventListener('mouseover', onMouseOver)
         el.addEventListener('mouseout', onMouseOut)
     })
 }
 
 function onMouseOver(event) {
-    // console.log('onMouseOver:', event)
+    // console.debug('onMouseOver:', event)
     mediaError.classList.add('d-none')
     mediaImage.classList.remove('d-none')
     if (event.pageY < window.innerHeight / 2) {
@@ -508,8 +729,6 @@ function onMouseOver(event) {
         mediaOuter.classList.remove('bottom-0')
         mediaOuter.classList.add('top-0')
     }
-    // console.log('name:', event.target.innerText)
-    // console.log('raw:', event.target.dataset.raw)
     const str = event.target.innerText
     const imageExtensions = /\.(gif|ico|jpeg|jpg|png|svg|webp)$/i
     if (str.match(imageExtensions)) {
@@ -520,13 +739,13 @@ function onMouseOver(event) {
         mediaOuter.classList.add('d-none')
         mediaImage.src = loadingImage
     }
-    // console.log('timeoutID:', timeoutID)
     if (timeoutID) {
         clearTimeout(timeoutID)
     }
 }
 
 function onMouseOut() {
+    // console.debug('onMouseOut')
     timeoutID = setTimeout(function () {
         mediaOuter.classList.add('d-none')
         mediaImage.src = loadingImage
diff --git a/src/js/service-worker.js b/src/js/service-worker.js
index 85904d6..d7260cc 100644
--- a/src/js/service-worker.js
+++ b/src/js/service-worker.js
@@ -83,7 +83,7 @@ async function contextMenusClicked(ctx) {
  * @param {String} notificationId
  */
 async function notificationsClicked(notificationId) {
-    console.log(`notifications.onClicked: ${notificationId}`)
+    console.debug(`notifications.onClicked: ${notificationId}`)
     chrome.notifications.clear(notificationId)
     if (notificationId.startsWith('http')) {
         await chrome.tabs.create({ active: true, url: notificationId })
@@ -97,7 +97,7 @@ async function notificationsClicked(notificationId) {
  * @param {String} namespace
  */
 function onChanged(changes, namespace) {
-    // console.log('onChanged:', changes, namespace)
+    // console.debug('onChanged:', changes, namespace)
     for (const [key, { oldValue, newValue }] of Object.entries(changes)) {
         if (key === 'options' && namespace === 'sync' && oldValue && newValue) {
             if (oldValue.contextMenu !== newValue.contextMenu) {
@@ -118,7 +118,7 @@ function onChanged(changes, namespace) {
  * @function createContextMenus
  */
 function createContextMenus() {
-    console.log('createContextMenus')
+    console.debug('createContextMenus')
     chrome.contextMenus.removeAll()
     const ctx = ['link', 'image', 'video', 'audio']
     const contexts = [
@@ -147,9 +147,9 @@ function createContextMenus() {
  * @return {Response}
  */
 async function postURL(endpoint, url) {
-    console.log(`postURL: "${endpoint}", "${url}"`)
+    console.debug(`postURL: "${endpoint}", "${url}"`)
     const { options } = await chrome.storage.sync.get(['options'])
-    console.log('options:', options)
+    console.debug('options:', options)
     if (!options?.siteUrl || !options?.authToken) {
         throw new Error('Missing URL or Token.')
     }
@@ -163,7 +163,7 @@ async function postURL(endpoint, url) {
     }
     const apiUrl = `${options.siteUrl}/api/${endpoint}/`
     const response = await fetch(apiUrl, opts)
-    console.log('response:', response)
+    console.debug('response:', response)
     return response
 }
 
@@ -175,18 +175,18 @@ async function postURL(endpoint, url) {
  * @param {String} message
  */
 async function processRemote(endpoint, url, message) {
-    console.log(`processRemote: "${endpoint}", "${url}", "${message}"`)
+    console.debug(`processRemote: "${endpoint}", "${url}", "${message}"`)
     let response
     try {
         response = await postURL(endpoint, url)
     } catch (e) {
-        console.log('error:', e)
+        console.info('error:', e)
         return await sendNotification('Fetch Error', `Error: ${error.message}`)
     }
     // console.log('response:', response)
     if (response.ok) {
         const data = await response.json()
-        console.log('data:', data)
+        console.debug('data:', data)
         await clipboardWrite(data.url)
         await sendNotification(message, data.url, data.url)
     } else {
@@ -195,7 +195,7 @@ async function processRemote(endpoint, url, message) {
             console.log('data:', data)
             await sendNotification('Processing Error', `Error: ${data.error}`)
         } catch (e) {
-            console.log('error:', e)
+            console.info('error:', e)
             await sendNotification(
                 'Processing Error',
                 `Error: Response Status: ${response.status}`
@@ -213,7 +213,7 @@ async function processRemote(endpoint, url, message) {
  * @param {Number} timeout - Optional
  */
 async function sendNotification(title, text, id = '', timeout = 10) {
-    console.log(`sendNotification: ${id || 'randomID'}: ${title} - ${text}`)
+    console.debug(`sendNotification: ${id || 'randomID'}: ${title} - ${text}`)
     const options = {
         type: 'basic',
         iconUrl: chrome.runtime.getURL('media/logo96.png'),