diff --git a/src/app.css b/src/app.css
index c82edbb468..f442bbbf5a 100644
--- a/src/app.css
+++ b/src/app.css
@@ -65,7 +65,7 @@ textarea::placeholder {
 }
 
 .input-prose {
-	@apply prose dark:prose-invert prose-headings:font-semibold prose-hr:my-4 prose-hr:border-gray-100 prose-hr:dark:border-gray-800 prose-p:my-1 prose-img:my-1 prose-headings:my-2 prose-pre:my-0 prose-table:my-0 prose-blockquote:my-0 prose-ul:my-1 prose-ol:my-1 prose-li:my-1 whitespace-pre-line;
+	@apply prose dark:prose-invert prose-headings:font-semibold prose-hr:my-4 prose-hr:border-gray-100 prose-hr:dark:border-gray-800 prose-p:my-1 prose-img:my-1 prose-headings:my-2 prose-pre:my-0 prose-table:my-0 prose-blockquote:my-0 prose-ul:my-1 prose-ol:my-1 prose-li:my-0.5 whitespace-pre-line;
 }
 
 .input-prose-sm {
@@ -337,7 +337,6 @@ input[type='number'] {
 
 	li {
 		align-items: start;
-
 		display: flex;
 
 		> label {
@@ -371,6 +370,96 @@ input[type='number'] {
 	ul[data-type='taskList'] {
 		margin: 0;
 	}
+
+	/* Reset nested regular ul elements to default styling */
+	ul:not([data-type='taskList']) {
+		list-style: disc;
+		padding-left: 1rem;
+
+		li {
+			align-items: initial;
+			display: list-item;
+
+			label {
+				flex: initial;
+				margin-right: initial;
+				margin-top: initial;
+				user-select: initial;
+				display: initial;
+			}
+
+			div {
+				flex: initial;
+				align-items: initial;
+			}
+		}
+	}
+}
+
+.input-prose .tiptap ul[data-type='taskList'] {
+	list-style: none;
+	margin-left: 0;
+	padding: 0;
+
+	li {
+		align-items: start;
+		display: flex;
+
+		> label {
+			flex: 0 0 auto;
+			margin-right: 0.5rem;
+			margin-top: 0.4rem;
+			user-select: none;
+			display: flex;
+		}
+
+		> div {
+			flex: 1 1 auto;
+
+			align-items: center;
+		}
+	}
+
+	/* checked data-checked="true" */
+
+	li[data-checked='true'] {
+		> div {
+			opacity: 0.5;
+			text-decoration: line-through;
+		}
+	}
+
+	input[type='checkbox'] {
+		cursor: pointer;
+	}
+
+	ul[data-type='taskList'] {
+		margin: 0;
+	}
+
+	/* Reset nested regular ul elements to default styling */
+	ul:not([data-type='taskList']) {
+		list-style: disc;
+		padding-left: 1rem;
+
+		li {
+			align-items: initial;
+			display: list-item;
+
+			label {
+				flex: initial;
+				margin-right: initial;
+				margin-top: initial;
+				user-select: initial;
+				display: initial;
+			}
+
+			div {
+				flex: initial;
+				align-items: initial;
+			}
+		}
+	}
 }
 
 @media (prefers-color-scheme: dark) {
diff --git a/src/lib/components/chat/Messages/Markdown/MarkdownTokens.svelte b/src/lib/components/chat/Messages/Markdown/MarkdownTokens.svelte
index 3fec5e2e6a..cc44ae80ea 100644
--- a/src/lib/components/chat/Messages/Markdown/MarkdownTokens.svelte
+++ b/src/lib/components/chat/Messages/Markdown/MarkdownTokens.svelte
@@ -222,7 +222,7 @@
 		{:else}
 			<ul dir="auto" class="">
 				{#each token.items as item, itemIdx}
-					<li class="text-start {item?.task ? 'flex -translate-x-7 gap-3.5 ' : ''}">
+					<li class="text-start {item?.task ? 'flex -translate-x-6.5 gap-3 ' : ''}">
 						{#if item?.task}
 							<input
 								class=""