diff --git a/desktop-app/resources/index.html b/desktop-app/resources/index.html
index 2cc02c25..ccc1b1fb 100644
--- a/desktop-app/resources/index.html
+++ b/desktop-app/resources/index.html
@@ -83,7 +83,7 @@ <h1 class="h4 mb-0 me-2">Markdown Viewer</h1>
                             <li><a class="dropdown-item" href="#" id="import-from-github"><i class="bi bi-github me-2"></i>From GitHub</a></li>
                         </ul>
                     </div>
-                    <input type="file" id="file-input" class="file-input" accept=".md,.markdown,text/markdown">
+                    <input type="file" id="file-input" class="file-input" accept=".md,.markdown,text/markdown" multiple>
                     
                     <div class="dropdown">
                         <button class="tool-button dropdown-toggle" type="button" id="exportDropdown" data-bs-toggle="dropdown" aria-expanded="false" title="Export Markdown">
@@ -1016,7 +1016,7 @@ <h3 class="modal-section-title">Open-source credits</h3>
         <div id="drag-overlay" class="drag-overlay" aria-hidden="true">
             <div class="drag-overlay-inner">
                 <i class="bi bi-cloud-arrow-up drag-overlay-icon"></i>
-                <p class="drag-overlay-text">Drop your Markdown file anywhere</p>
+                <p class="drag-overlay-text">Drop your Markdown files anywhere</p>
                 <p class="drag-overlay-sub">.md or .markdown files supported</p>
             </div>
         </div>
@@ -1039,7 +1039,7 @@ <h3 class="modal-section-title">Open-source credits</h3>
                 </div>
                 <textarea id="markdown-editor" placeholder="Type or paste your Markdown here..."></textarea>
                 <div class="drop-hint" aria-hidden="true">
-                    <i class="bi bi-cloud-arrow-up me-1"></i>Drop a .md file anywhere to open it
+                    <i class="bi bi-cloud-arrow-up me-1"></i>Drop .md files anywhere to open them
                 </div>
             </div>
             <!-- Resize Divider - Story 1.3 -->
diff --git a/desktop-app/resources/js/script.js b/desktop-app/resources/js/script.js
index f4b92207..531892ba 100644
--- a/desktop-app/resources/js/script.js
+++ b/desktop-app/resources/js/script.js
@@ -4453,31 +4453,75 @@ document.addEventListener("DOMContentLoaded", async function () {
     }
   }
 
+  function isMarkdownFile(file) {
+    return Boolean(file) && (
+      file.type === "text/markdown" ||
+      /\.(md|markdown)$/i.test(file.name || "")
+    );
+  }
+
+  function getMarkdownFileTitle(file) {
+    return (file && file.name ? file.name : "document.md").replace(/\.(md|markdown)$/i, "");
+  }
+
   function importMarkdownFile(file) {
-    if (file.size > 10 * 1024 * 1024) {
-      alert('File is too large (maximum 10MB supported).');
-      return;
-    }
+    return new Promise(function(resolve) {
+      if (!file) {
+        resolve(false);
+        return;
+      }
+
+      if (file.size > 10 * 1024 * 1024) {
+        alert('File is too large (maximum 10MB supported).');
+        resolve(false);
+        return;
+      }
 
-    const reader = new FileReader();
-    reader.onload = function(e) {
-      const text = e.target.result || '';
+      const reader = new FileReader();
+      reader.onload = function(e) {
+        const text = e.target.result || '';
       
-      // Simple binary check: look for null bytes in the first 8KB
-      const checkLength = Math.min(text.length, 8000);
-      for (let i = 0; i < checkLength; i++) {
-        if (text.charCodeAt(i) === 0) {
-          alert('Cannot import: The selected file appears to be a binary file.');
-          return;
+        // Simple binary check: look for null bytes in the first 8KB
+        const checkLength = Math.min(text.length, 8000);
+        for (let i = 0; i < checkLength; i++) {
+          if (text.charCodeAt(i) === 0) {
+            alert('Cannot import: The selected file appears to be a binary file.');
+            resolve(false);
+            return;
+          }
         }
+
+        newTab(text, getMarkdownFileTitle(file));
+        resolve(true);
+      };
+      reader.onerror = function() {
+        alert('Failed to read the file. Please check permissions and try again.');
+        resolve(false);
+      };
+      reader.readAsText(file);
+    });
+  }
+
+  async function importMarkdownFiles(fileList, options) {
+    const settings = options || {};
+    const files = Array.from(fileList || []);
+    const markdownFiles = files.filter(isMarkdownFile);
+
+    if (!markdownFiles.length) {
+      if (settings.showInvalidAlert !== false) {
+        alert("Please upload Markdown files (.md or .markdown)");
       }
+      return 0;
+    }
 
-      newTab(text, file.name.replace(/\.md$/i, ''));
-    };
-    reader.onerror = function() {
-      alert('Failed to read the file. Please check permissions and try again.');
-    };
-    reader.readAsText(file);
+    let importedCount = 0;
+    for (const file of markdownFiles) {
+      if (await importMarkdownFile(file)) {
+        importedCount++;
+      }
+    }
+
+    return importedCount;
   }
 
   function isMarkdownPath(path) {
@@ -9879,12 +9923,12 @@ document.addEventListener("DOMContentLoaded", async function () {
     });
   }
 
-  fileInput.addEventListener("change", function (e) {
-    const file = e.target.files[0];
-    if (file) {
-      importMarkdownFile(file);
+  fileInput.addEventListener("change", async function (e) {
+    try {
+      await importMarkdownFiles(e.target.files);
+    } finally {
+      this.value = "";
     }
-    this.value = "";
   });
 
   exportMd.addEventListener("click", function () {
@@ -14235,19 +14279,11 @@ document.addEventListener("DOMContentLoaded", async function () {
     handleDrop(e);
   }, false);
 
-  function handleDrop(e) {
+  async function handleDrop(e) {
     const dt = e.dataTransfer;
-    const files = dt.files;
-    if (files.length) {
-      const file = files[0];
-      const isMarkdownFile =
-        file.type === "text/markdown" ||
-        /\.(md|markdown)$/i.test(file.name || "");
-      if (isMarkdownFile) {
-        importMarkdownFile(file);
-      } else {
-        alert("Please upload a Markdown file (.md or .markdown)");
-      }
+    const files = dt && dt.files;
+    if (files && files.length) {
+      await importMarkdownFiles(files);
     }
   }
 
diff --git a/index.html b/index.html
index 84ca63d4..af299eb7 100644
--- a/index.html
+++ b/index.html
@@ -167,7 +167,7 @@ <h1 class="h4 mb-0 me-2">Markdown Viewer</h1>
                             <li><a class="dropdown-item" href="#" id="import-from-github"><i class="bi bi-github me-2"></i>From GitHub</a></li>
                         </ul>
                     </div>
-                    <input type="file" id="file-input" class="file-input" accept=".md,.markdown,text/markdown">
+                    <input type="file" id="file-input" class="file-input" accept=".md,.markdown,text/markdown" multiple>
                     
                     <div class="dropdown">
                         <button class="tool-button dropdown-toggle" type="button" id="exportDropdown" data-bs-toggle="dropdown" aria-expanded="false" title="Export Markdown">
@@ -1100,7 +1100,7 @@ <h3 class="modal-section-title">Open-source credits</h3>
         <div id="drag-overlay" class="drag-overlay" aria-hidden="true">
             <div class="drag-overlay-inner">
                 <i class="bi bi-cloud-arrow-up drag-overlay-icon"></i>
-                <p class="drag-overlay-text">Drop your Markdown file anywhere</p>
+                <p class="drag-overlay-text">Drop your Markdown files anywhere</p>
                 <p class="drag-overlay-sub">.md or .markdown files supported</p>
             </div>
         </div>
@@ -1123,7 +1123,7 @@ <h3 class="modal-section-title">Open-source credits</h3>
                 </div>
                 <textarea id="markdown-editor" placeholder="Type, paste, or import Markdown here..." aria-label="Markdown editor input with live preview"></textarea>
                 <div class="drop-hint" aria-hidden="true">
-                    <i class="bi bi-cloud-arrow-up me-1"></i>Drop a .md file anywhere to open it
+                    <i class="bi bi-cloud-arrow-up me-1"></i>Drop .md files anywhere to open them
                 </div>
             </div>
             <!-- Resize Divider - Story 1.3 -->
diff --git a/script.js b/script.js
index beb0ae99..46d14b9b 100644
--- a/script.js
+++ b/script.js
@@ -4684,31 +4684,75 @@ ${selector} .arrowheadPath {
     }
   }
 
+  function isMarkdownFile(file) {
+    return Boolean(file) && (
+      file.type === "text/markdown" ||
+      /\.(md|markdown)$/i.test(file.name || "")
+    );
+  }
+
+  function getMarkdownFileTitle(file) {
+    return (file && file.name ? file.name : "document.md").replace(/\.(md|markdown)$/i, "");
+  }
+
   function importMarkdownFile(file) {
-    if (file.size > 10 * 1024 * 1024) {
-      alert('File is too large (maximum 10MB supported).');
-      return;
-    }
+    return new Promise(function(resolve) {
+      if (!file) {
+        resolve(false);
+        return;
+      }
+
+      if (file.size > 10 * 1024 * 1024) {
+        alert('File is too large (maximum 10MB supported).');
+        resolve(false);
+        return;
+      }
 
-    const reader = new FileReader();
-    reader.onload = function(e) {
-      const text = e.target.result || '';
+      const reader = new FileReader();
+      reader.onload = function(e) {
+        const text = e.target.result || '';
       
-      // Simple binary check: look for null bytes in the first 8KB
-      const checkLength = Math.min(text.length, 8000);
-      for (let i = 0; i < checkLength; i++) {
-        if (text.charCodeAt(i) === 0) {
-          alert('Cannot import: The selected file appears to be a binary file.');
-          return;
+        // Simple binary check: look for null bytes in the first 8KB
+        const checkLength = Math.min(text.length, 8000);
+        for (let i = 0; i < checkLength; i++) {
+          if (text.charCodeAt(i) === 0) {
+            alert('Cannot import: The selected file appears to be a binary file.');
+            resolve(false);
+            return;
+          }
         }
+
+        newTab(text, getMarkdownFileTitle(file));
+        resolve(true);
+      };
+      reader.onerror = function() {
+        alert('Failed to read the file. Please check permissions and try again.');
+        resolve(false);
+      };
+      reader.readAsText(file);
+    });
+  }
+
+  async function importMarkdownFiles(fileList, options) {
+    const settings = options || {};
+    const files = Array.from(fileList || []);
+    const markdownFiles = files.filter(isMarkdownFile);
+
+    if (!markdownFiles.length) {
+      if (settings.showInvalidAlert !== false) {
+        alert("Please upload Markdown files (.md or .markdown)");
       }
+      return 0;
+    }
 
-      newTab(text, file.name.replace(/\.md$/i, ''));
-    };
-    reader.onerror = function() {
-      alert('Failed to read the file. Please check permissions and try again.');
-    };
-    reader.readAsText(file);
+    let importedCount = 0;
+    for (const file of markdownFiles) {
+      if (await importMarkdownFile(file)) {
+        importedCount++;
+      }
+    }
+
+    return importedCount;
   }
 
   function isMarkdownPath(path) {
@@ -10110,12 +10154,12 @@ ${selector} .arrowheadPath {
     });
   }
 
-  fileInput.addEventListener("change", function (e) {
-    const file = e.target.files[0];
-    if (file) {
-      importMarkdownFile(file);
+  fileInput.addEventListener("change", async function (e) {
+    try {
+      await importMarkdownFiles(e.target.files);
+    } finally {
+      this.value = "";
     }
-    this.value = "";
   });
 
   exportMd.addEventListener("click", function () {
@@ -14466,19 +14510,11 @@ ${selector} .arrowheadPath {
     handleDrop(e);
   }, false);
 
-  function handleDrop(e) {
+  async function handleDrop(e) {
     const dt = e.dataTransfer;
-    const files = dt.files;
-    if (files.length) {
-      const file = files[0];
-      const isMarkdownFile =
-        file.type === "text/markdown" ||
-        /\.(md|markdown)$/i.test(file.name || "");
-      if (isMarkdownFile) {
-        importMarkdownFile(file);
-      } else {
-        alert("Please upload a Markdown file (.md or .markdown)");
-      }
+    const files = dt && dt.files;
+    if (files && files.length) {
+      await importMarkdownFiles(files);
     }
   }