diff --git a/supervisor/shared/web_workflow/static/directory.html b/supervisor/shared/web_workflow/static/directory.html
index b88e74684b..6e2b833d6f 100644
--- a/supervisor/shared/web_workflow/static/directory.html
+++ b/supervisor/shared/web_workflow/static/directory.html
@@ -11,8 +11,8 @@
     <h1><a href="/"><img src="/favicon.ico"/></a>&nbsp;<span id="path"></span></h1>
     <div id="usbwarning" style="display: none;">🛈 USB is using the storage. Only allowing reads. See <a href="https://learn.adafruit.com/circuitpython-essentials/circuitpython-storage">the CircuitPython Essentials: Storage guide</a> for details.</div>
     <template id="row"><tr><td></td><td></td><td><a></a></td><td></td><td><button class="delete">🗑️</button></td><td><a class="edit_link" href="">Edit</a></td></tr></template>
-    <table>
-        <thead><tr><th>Type</th><th>Size</th><th>Path</th><th>Modified</th><th></th></tr></thead>
+    <table class="sortable">
+        <thead><tr><th>Type</th><th>Size</th><th aria-sort="ascending"><button>Path<span aria-hidden="true"></span></button></th><th>Modified</th><th></th></tr></thead>
         <tbody></tbody>
     </table>
     <hr>
diff --git a/supervisor/shared/web_workflow/static/directory.js b/supervisor/shared/web_workflow/static/directory.js
index 91389343d6..657a8169d4 100644
--- a/supervisor/shared/web_workflow/static/directory.js
+++ b/supervisor/shared/web_workflow/static/directory.js
@@ -1,3 +1,172 @@
+/*
+ *   This content is licensed according to the W3C Software License at
+ *   https://www.w3.org/Consortium/Legal/2015/copyright-software-and-document
+ *
+ *   File:   sortable-table.js
+ *
+ *   Desc:   Adds sorting to a HTML data table that implements ARIA Authoring Practices
+ */
+
+'use strict';
+
+class SortableTable {
+  constructor(tableNode) {
+    this.tableNode = tableNode;
+
+    this.columnHeaders = tableNode.querySelectorAll('thead th');
+
+    this.sortColumns = [];
+
+    for (var i = 0; i < this.columnHeaders.length; i++) {
+      var ch = this.columnHeaders[i];
+      var buttonNode = ch.querySelector('button');
+      if (buttonNode) {
+        this.sortColumns.push(i);
+        buttonNode.setAttribute('data-column-index', i);
+        buttonNode.addEventListener('click', this.handleClick.bind(this));
+      }
+    }
+
+    this.optionCheckbox = document.querySelector(
+      'input[type="checkbox"][value="show-unsorted-icon"]'
+    );
+
+    if (this.optionCheckbox) {
+      this.optionCheckbox.addEventListener(
+        'change',
+        this.handleOptionChange.bind(this)
+      );
+      if (this.optionCheckbox.checked) {
+        this.tableNode.classList.add('show-unsorted-icon');
+      }
+    }
+  }
+
+  setColumnHeaderSort(columnIndex) {
+    if (typeof columnIndex === 'string') {
+      columnIndex = parseInt(columnIndex);
+    }
+
+    for (var i = 0; i < this.columnHeaders.length; i++) {
+      var ch = this.columnHeaders[i];
+      var buttonNode = ch.querySelector('button');
+      if (i === columnIndex) {
+        var value = ch.getAttribute('aria-sort');
+        if (value === 'descending') {
+          ch.setAttribute('aria-sort', 'ascending');
+          this.sortColumn(
+            columnIndex,
+            'ascending',
+            ch.classList.contains('num')
+          );
+        } else {
+          ch.setAttribute('aria-sort', 'descending');
+          this.sortColumn(
+            columnIndex,
+            'descending',
+            ch.classList.contains('num')
+          );
+        }
+      } else {
+        if (ch.hasAttribute('aria-sort') && buttonNode) {
+          ch.removeAttribute('aria-sort');
+        }
+      }
+    }
+  }
+
+  sortColumn(columnIndex, sortValue, isNumber) {
+    function compareValues(a, b) {
+      if (sortValue === 'ascending') {
+        if (a.value === b.value) {
+          return 0;
+        } else {
+          if (isNumber) {
+            return a.value - b.value;
+          } else {
+            return a.value < b.value ? -1 : 1;
+          }
+        }
+      } else {
+        if (a.value === b.value) {
+          return 0;
+        } else {
+          if (isNumber) {
+            return b.value - a.value;
+          } else {
+            return a.value > b.value ? -1 : 1;
+          }
+        }
+      }
+    }
+
+    if (typeof isNumber !== 'boolean') {
+      isNumber = false;
+    }
+
+    var tbodyNode = this.tableNode.querySelector('tbody');
+    var rowNodes = [];
+    var dataCells = [];
+
+    var rowNode = tbodyNode.firstElementChild;
+
+    var index = 0;
+    while (rowNode) {
+      rowNodes.push(rowNode);
+      var rowCells = rowNode.querySelectorAll('th, td');
+      var dataCell = rowCells[columnIndex];
+
+      var data = {};
+      data.index = index;
+      data.value = dataCell.textContent.toLowerCase().trim();
+      if (isNumber) {
+        data.value = parseFloat(data.value);
+      }
+      dataCells.push(data);
+      rowNode = rowNode.nextElementSibling;
+      index += 1;
+    }
+
+    dataCells.sort(compareValues);
+
+    // remove rows
+    while (tbodyNode.firstChild) {
+      tbodyNode.removeChild(tbodyNode.lastChild);
+    }
+
+    // add sorted rows
+    for (var i = 0; i < dataCells.length; i += 1) {
+      tbodyNode.appendChild(rowNodes[dataCells[i].index]);
+    }
+  }
+
+  /* EVENT HANDLERS */
+
+  handleClick(event) {
+    var tgt = event.currentTarget;
+    this.setColumnHeaderSort(tgt.getAttribute('data-column-index'));
+  }
+
+  handleOptionChange(event) {
+    var tgt = event.currentTarget;
+
+    if (tgt.checked) {
+      this.tableNode.classList.add('show-unsorted-icon');
+    } else {
+      this.tableNode.classList.remove('show-unsorted-icon');
+    }
+  }
+}
+
+// Initialize sortable table buttons
+window.addEventListener('load', function () {
+  var sortableTables = document.querySelectorAll('table.sortable');
+  for (var i = 0; i < sortableTables.length; i++) {
+    new SortableTable(sortableTables[i]);
+  }
+});
+
+
 let new_directory_name = document.getElementById("name");
 let files = document.getElementById("files");