diff --git a/src/lib/elements/element_input_files_tbl.svelte b/src/lib/elements/element_input_files_tbl.svelte
index c05155a0..83b873f2 100644
--- a/src/lib/elements/element_input_files_tbl.svelte
+++ b/src/lib/elements/element_input_files_tbl.svelte
@@ -175,16 +175,19 @@ async function process_file_list(file_list: FileList) {
             warning_legacy_extension = true;
             if (guessed_extension == 'ppt') {
                 warning_message =
-                    'It appears this is a legacy PowerPoint file and has not been officially supported since Office PowerPoint 2003. This file is known to have issues and may not work well. It is <strong>strongly</strong> recommended that this file be saved using the modern PPTX format.';
+                    '<strong>WARNING</strong>: It appears this is a legacy Microsoft PowerPoint file and has not been officially supported since Office PowerPoint <strong>2003</strong>. This file type is known to have issues and may not work well. It is <strong>strongly</strong> recommended that this file be saved using the modern PPTX format in PowerPoint. <a href="https://support.microsoft.com/en-us/office/saving-ppt-to-pptx-or-pptm-e8ebc946-98d1-41bb-bb3e-cf00c65e3a55" class="underline font-semibold text-sm">More Help?</a>';
+            } else if (guessed_extension == 'doc') {
+                warning_message =
+                    '<strong>WARNING</strong>: It appears this is a legacy Microsoft Word Document file and has not been officially supported since Office Word <strong>2003</strong>. This file type is known to have issues and may not work well. It is <strong>strongly</strong> recommended that this file be saved using the modern DOCX format in Word. <a href="https://support.microsoft.com/en-us/office/saving-doc-to-docx-or-dorm-0107099d-dc1e-4897-8851-f8c9f483f7cd" class="underline font-semibold text-sm">More Help?</a>';
             } else if (guessed_extension == 'avi') {
                 warning_message =
-                    'It appears this is a video file using the AVI format. It is <strong>strongly</strong> recommended that this file be re-saved as an MP4, MOV, MKV, or MPG/MPEG. The file will also likely be much smaller.';
+                    '<strong>WARNING</strong>: It appears this is a video file using the AVI format. It is <strong>strongly</strong> recommended that this file be re-saved as an MP4, MOV, MKV, or MPG/MPEG. The file will also likely be much smaller.';
             } else if (guessed_extension == 'wmv') {
                 warning_message =
-                    "It appears this is a video file using Microsoft's WMV format. It is <strong>strongly</strong> recommended that this file be re-saved as an MP4, MOV, MKV, or MPG/MPEG.";
+                    "<strong>WARNING</strong>: It appears this is a video file using Microsoft's WMV format. It is <strong>strongly</strong> recommended that this file be re-saved as an MP4, MOV, MKV, or MPG/MPEG.";
             } else {
                 warning_message =
-                    'It appears this is a legacy or not very well supported file format. It is <strong>strongly</strong> recommended that it be saved in an alternative format if possible.';
+                    '<strong>WARNING</strong>: It appears this is a legacy or not very well supported file format. It is <strong>strongly</strong> recommended that it be saved in an alternative format if possible.';
             }
         } else if (file_size_bytes > 52428800) {
             // 50 MB = 52428800 bytes
@@ -217,7 +220,7 @@ async function process_file_list(file_list: FileList) {
 
         // .ppt and .doc must be converted before upload — block, don't just warn
         file_data['block_upload'] =
-            guessed_extension === 'ppt' || guessed_extension === 'doc';
+            guessed_extension === 'ppt' || guessed_extension === 'doc' || guessed_extension === 'xls';
 
         file_data['uploaded'] = null;
         file_data['uploaded_bytes'] = null;
@@ -277,7 +280,7 @@ async function process_file_list(file_list: FileList) {
     }
 
     const has_blocked = processed_file_list.some((f) => f.block_upload);
-    file_list_status = has_blocked ? 'blocked_legacy' : 'ready';
+    file_list_status = has_blocked && !$ae_loc.trusted_access ? 'blocked_legacy' : 'ready';
     console.log(processed_file_list);
 
     // return JSON.parse(JSON.stringify(processed_file_list));
@@ -369,7 +372,7 @@ run(() => {
     {#if file_list_status == 'blocked_legacy'}
         <div class="m-1 rounded-md border-2 border-red-500 bg-red-100 p-3 text-sm text-red-800 dark:bg-red-900/30 dark:text-red-200">
             <strong>⚠ Upload blocked — legacy file format detected.</strong>
-            Please remove the flagged file(s) below and re-save in the modern format before uploading.
+            This Microsoft file type has not been supported in more than 10 years. Please remove the flagged file(s) below and re-save in the modern format before uploading.
         </div>
     {/if}
 
@@ -380,18 +383,18 @@ run(() => {
         <table class="slct_file_list text-sm {table_class_li.join(' ')}">
             <thead>
                 <tr>
-                    <th>Remove</th>
-                    <th>Filename</th>
-                    <th>Modified</th>
-                    <th>Size</th>
+                    <th class="text-xs">Remove</th>
+                    <th class="text-xs">Filename</th>
+                    <th class="text-xs">Modified</th>
+                    <th class="text-xs">Size</th>
                     <!-- <th>Type</th> -->
-                    <th>Ext</th>
-                    <th>Hash</th>
+                    <th class="text-xs">Ext</th>
+                    <th class="text-xs">Hash</th>
                 </tr>
             </thead>
             {#each processed_file_list as file_list_item, file_index (file_index)}
                 <tbody>
-                    <tr>
+                    <tr class="border">
                         <td class="file_remove">
                             <button
                                 onclick={preventDefault(() => {
@@ -441,7 +444,7 @@ run(() => {
                     {#if file_list_item.warning_message}
                         <tr>
                             <td colspan="6"
-                                class="text-left text-xs"
+                                class="text-left text-xs m-1 border border-red-500 p-3"
                                 class:bg-red-100={file_list_item.block_upload}
                                 class:text-red-800={file_list_item.block_upload}
                                 class:bg-yellow-50={!file_list_item.block_upload}
diff --git a/src/lib/elements/element_manage_event_file_li.svelte b/src/lib/elements/element_manage_event_file_li.svelte
index f1a02795..a10679c8 100644
--- a/src/lib/elements/element_manage_event_file_li.svelte
+++ b/src/lib/elements/element_manage_event_file_li.svelte
@@ -37,6 +37,7 @@ import {
     Laptop,
     LoaderCircle,
     Monitor,
+    OctagonAlert,
     Pencil,
     RefreshCw,
     Save,
@@ -715,14 +716,24 @@ async function handle_convert_pdf_to_image(event_file_obj: key_val) {
                                     <span
                                         class="flex w-full flex-col justify-between lg:flex-row">
                                         <span
+                                            class:preset-tonal-error={event_file_obj.extension == 'doc' || event_file_obj.extension == 'ppt' || event_file_obj.extension == 'xls'}
                                             class:hidden={display_mode !=
-                                                'default'}>
+                                                'default'}
+                                            title={(event_file_obj.extension == 'doc' || event_file_obj.extension == 'ppt' || event_file_obj.extension == 'xls') ? `WARNING: Microsoft 2003 legacy file type. Please resave this in a modern PowerPoint, Word, or Excel format!\nFile type = ${event_file_obj.extension}\nContent type = ${event_file_obj.content_type}` : `File type = ${event_file_obj.extension}\nContent type = ${event_file_obj.content_type}`}
+                                            >
                                             Type:
                                             <strong
-                                                >{event_file_obj.extension}
+                                                >
                                                 <ExtIcon
                                                     size="1em"
                                                     class="inline-block" />
+                                                {event_file_obj.extension}
+                                                {#if event_file_obj.extension == 'doc' || event_file_obj.extension == 'ppt' || event_file_obj.extension == 'xls'}
+                                                <!-- Legacy warning icon -->
+                                                <OctagonAlert
+                                                    size="1em"
+                                                    class="inline-block" />
+                                                {/if}
                                             </strong>
                                             <!-- {#if event_file_obj.open_in_os == 'win'}
                 <strong>