diff --git a/webview-ui/src/components/common/MarkdownBlock.tsx b/webview-ui/src/components/common/MarkdownBlock.tsx
index 37a0278991..91e129ceb2 100644
--- a/webview-ui/src/components/common/MarkdownBlock.tsx
+++ b/webview-ui/src/components/common/MarkdownBlock.tsx
@@ -50,6 +50,44 @@ const remarkUrlToLink = () => {
 	}
 }
 
+/**
+ * Custom remark plugin that prevents filenames with extensions from being parsed as bold text
+ * For example: __init__.py should not be rendered as bold "init" followed by ".py"
+ * Solves https://github.com/cline/cline/issues/1028
+ */
+const remarkPreventBoldFilenames = () => {
+	return (tree: any) => {
+		visit(tree, "strong", (node: any, index: number | undefined, parent: any) => {
+			// Only process if there's a next node (potential file extension)
+			if (!parent || typeof index === "undefined" || index === parent.children.length - 1) return
+
+			const nextNode = parent.children[index + 1]
+
+			// Check if next node is text and starts with . followed by extension
+			if (nextNode.type !== "text" || !nextNode.value.match(/^\.[a-zA-Z0-9]+/)) return
+
+			// If the strong node has multiple children, something weird is happening
+			if (node.children?.length !== 1) return
+
+			// Get the text content from inside the strong node
+			const strongContent = node.children?.[0]?.value
+			if (!strongContent || typeof strongContent !== "string") return
+
+			// Validate that the strong content is a valid filename
+			if (!strongContent.match(/^[a-zA-Z0-9_-]+$/)) return
+
+			// Combine into a single text node
+			const newNode = {
+				type: "text",
+				value: `__${strongContent}__${nextNode.value}`,
+			}
+
+			// Replace both nodes with the combined text node
+			parent.children.splice(index, 2, newNode)
+		})
+	}
+}
+
 const StyledMarkdown = styled.div`
 	pre {
 		background-color: ${CODE_BLOCK_BG_COLOR};
@@ -160,6 +198,7 @@ const MarkdownBlock = memo(({ markdown }: MarkdownBlockProps) => {
 	const { theme } = useExtensionState()
 	const [reactContent, setMarkdown] = useRemark({
 		remarkPlugins: [
+			remarkPreventBoldFilenames,
 			remarkUrlToLink,
 			() => {
 				return (tree) => {