diff --git a/src/apps/officer-web/styles/prose.css b/src/apps/officer-web/styles/prose.css
index a45c32dc..ff4b86ba 100644
--- a/src/apps/officer-web/styles/prose.css
+++ b/src/apps/officer-web/styles/prose.css
@@ -36,7 +36,9 @@
   margin: 1em 0 0.3em;
 }
 
-.chat-md h4, .chat-md h5, .chat-md h6 {
+.chat-md h4,
+.chat-md h5,
+.chat-md h6 {
   font-size: 1em;
   font-weight: 600;
   margin: 0.8em 0 0.25em;
@@ -69,9 +71,46 @@
   color: hsl(var(--muted-foreground));
 }
 
-.chat-md ul, .chat-md ol {
+/* Tailwind's preflight resets `list-style: none` on every ul/ol, so a list rendered here had the
+   indent but no bullets and — more confusingly — no NUMBERS: an ordered list read as an unordered
+   pile of lines, and copying the same text elsewhere showed it numbered correctly, which makes it
+   look like the model emitted bad markdown rather than the stylesheet eating the markers. The
+   `li::marker` rule below was colouring a marker that was never drawn. */
+.chat-md ul,
+.chat-md ol {
   margin: 0.5em 0;
   padding-left: 1.5em;
+  list-style-position: outside;
+}
+
+.chat-md ul {
+  list-style-type: disc;
+}
+
+.chat-md ol {
+  list-style-type: decimal;
+}
+
+/* Nested levels, following the usual typographic convention so depth stays readable. */
+.chat-md ul ul {
+  list-style-type: circle;
+}
+
+.chat-md ul ul ul {
+  list-style-type: square;
+}
+
+.chat-md ol ol {
+  list-style-type: lower-alpha;
+}
+
+.chat-md ol ol ol {
+  list-style-type: lower-roman;
+}
+
+/* A task list carries its own checkbox; a bullet next to it is noise. */
+.chat-md li:has(> input[type='checkbox']) {
+  list-style-type: none;
 }
 
 .chat-md li {
@@ -147,7 +186,7 @@
   margin: 0.75em 0;
 }
 
-.chat-md input[type="checkbox"] {
+.chat-md input[type='checkbox'] {
   accent-color: var(--duck-teal);
   margin-right: 0.4em;
 }
@@ -185,7 +224,9 @@
   margin: 1.2em 0 0.4em;
 }
 
-.file-viewer-md h4, .file-viewer-md h5, .file-viewer-md h6 {
+.file-viewer-md h4,
+.file-viewer-md h5,
+.file-viewer-md h6 {
   color: hsl(var(--foreground));
   font-size: 1.05em;
   font-weight: 600;
@@ -219,9 +260,31 @@
   color: hsl(var(--muted-foreground));
 }
 
-.file-viewer-md ul, .file-viewer-md ol {
+.file-viewer-md ul,
+.file-viewer-md ol {
   margin: 0.75em 0;
   padding-left: 1.75em;
+  list-style-position: outside;
+}
+
+.file-viewer-md ul {
+  list-style-type: disc;
+}
+
+.file-viewer-md ol {
+  list-style-type: decimal;
+}
+
+.file-viewer-md ul ul {
+  list-style-type: circle;
+}
+
+.file-viewer-md ol ol {
+  list-style-type: lower-alpha;
+}
+
+.file-viewer-md li:has(> input[type='checkbox']) {
+  list-style-type: none;
 }
 
 .file-viewer-md li {
@@ -270,7 +333,7 @@
   margin: 1em 0;
 }
 
-.file-viewer-md input[type="checkbox"] {
+.file-viewer-md input[type='checkbox'] {
   accent-color: var(--duck-teal);
   margin-right: 0.5em;
 }
@@ -308,7 +371,9 @@
   margin: 1.2em 0 0.4em;
 }
 
-.skill-md h4, .skill-md h5, .skill-md h6 {
+.skill-md h4,
+.skill-md h5,
+.skill-md h6 {
   color: hsl(var(--foreground));
   font-size: 1.05em;
   font-weight: 600;
@@ -342,9 +407,31 @@
   color: hsl(var(--muted-foreground));
 }
 
-.skill-md ul, .skill-md ol {
+.skill-md ul,
+.skill-md ol {
   margin: 0.75em 0;
   padding-left: 1.75em;
+  list-style-position: outside;
+}
+
+.skill-md ul {
+  list-style-type: disc;
+}
+
+.skill-md ol {
+  list-style-type: decimal;
+}
+
+.skill-md ul ul {
+  list-style-type: circle;
+}
+
+.skill-md ol ol {
+  list-style-type: lower-alpha;
+}
+
+.skill-md li:has(> input[type='checkbox']) {
+  list-style-type: none;
 }
 
 .skill-md li {
@@ -420,7 +507,7 @@
   margin: 1em 0;
 }
 
-.skill-md input[type="checkbox"] {
+.skill-md input[type='checkbox'] {
   accent-color: var(--duck-teal);
   margin-right: 0.5em;
 }
diff --git a/src/workspaces/components/MarkdownEditor.tsx b/src/workspaces/components/MarkdownEditor.tsx
index 715fbbd3..be3c14dd 100644
--- a/src/workspaces/components/MarkdownEditor.tsx
+++ b/src/workspaces/components/MarkdownEditor.tsx
@@ -83,7 +83,13 @@ export function MarkdownEditor({
                    .markdown-preview h2 { font-size: 1.5rem; font-weight: bold; margin: 1.25rem 0 0.75rem 0; }
                    .markdown-preview h3 { font-size: 1.25rem; font-weight: bold; margin: 1rem 0 0.5rem 0; }
                    .markdown-preview p { margin: 0.75rem 0; line-height: 1.6; }
-                   .markdown-preview ul, .markdown-preview ol { margin: 1rem 0; padding-left: 2rem; }
+                   /* list-style is restored explicitly — tailwind preflight strips it, which leaves an
+                      ordered list indented but unnumbered. */
+                   .markdown-preview ul, .markdown-preview ol { margin: 1rem 0; padding-left: 2rem; list-style-position: outside; }
+                   .markdown-preview ul { list-style-type: disc; }
+                   .markdown-preview ol { list-style-type: decimal; }
+                   .markdown-preview ul ul { list-style-type: circle; }
+                   .markdown-preview ol ol { list-style-type: lower-alpha; }
                    .markdown-preview li { margin: 0.5rem 0; line-height: 1.6; }
                    .markdown-preview code { background-color: rgb(229, 229, 229); color: rgb(31, 41, 55); padding: 0.25rem 0.5rem; border-radius: 0.25rem; font-size: 0.875rem; }
                    .markdown-preview pre { background-color: rgb(17, 24, 39); color: rgb(243, 244, 246); padding: 1rem; border-radius: 0.5rem; overflow-x: auto; margin: 1rem 0; }