diff --git a/packages/ui/src/features/sessions/components/session-update/parseFileMentions.test.tsx b/packages/ui/src/features/sessions/components/session-update/parseFileMentions.test.tsx
new file mode 100644
index 0000000000..011d701748
--- /dev/null
+++ b/packages/ui/src/features/sessions/components/session-update/parseFileMentions.test.tsx
@@ -0,0 +1,46 @@
+import { Theme } from "@radix-ui/themes";
+import { render, screen } from "@testing-library/react";
+import { describe, expect, it } from "vitest";
+import { hasFileMentions, parseFileMentions } from "./parseFileMentions";
+
+function renderParts(content: string) {
+  return render(<Theme>{parseFileMentions(content)}</Theme>);
+}
+
+describe("parseFileMentions", () => {
+  it("highlights a leading slash command", () => {
+    renderParts("/deploy the app");
+    expect(screen.getByText("/deploy")).toBeInTheDocument();
+  });
+
+  it("highlights every slash command, not just the first", () => {
+    // A submitted prompt using several skills arrives with its <skill /> tags
+    // already flattened to plain /name text.
+    renderParts("/first do a thing then /second and finally /third");
+    expect(screen.getByText("/first")).toBeInTheDocument();
+    expect(screen.getByText("/second")).toBeInTheDocument();
+    expect(screen.getByText("/third")).toBeInTheDocument();
+  });
+
+  it("highlights a slash command that is not at the start of the string", () => {
+    renderParts("please run /cleanup now");
+    expect(screen.getByText("/cleanup")).toBeInTheDocument();
+  });
+
+  it("does not treat a mid-word slash as a command", () => {
+    renderParts("check the and/or logic");
+    expect(screen.queryByText("/or")).not.toBeInTheDocument();
+  });
+
+  it("renders slash commands alongside file mentions", () => {
+    renderParts('/review <file path="src/app/main.ts" /> then /ship');
+    expect(screen.getByText("/review")).toBeInTheDocument();
+    expect(screen.getByText("app/main.ts")).toBeInTheDocument();
+    expect(screen.getByText("/ship")).toBeInTheDocument();
+  });
+
+  it("detects slash commands anywhere for hasFileMentions", () => {
+    expect(hasFileMentions("run /skill please")).toBe(true);
+    expect(hasFileMentions("no commands here")).toBe(false);
+  });
+});
diff --git a/packages/ui/src/features/sessions/components/session-update/parseFileMentions.tsx b/packages/ui/src/features/sessions/components/session-update/parseFileMentions.tsx
index f50e9bde9d..714d84a966 100644
--- a/packages/ui/src/features/sessions/components/session-update/parseFileMentions.tsx
+++ b/packages/ui/src/features/sessions/components/session-update/parseFileMentions.tsx
@@ -15,7 +15,12 @@ const MENTION_TAG_REGEX =
   /<file\s+path="([^"]+)"\s*\/>|<(github_issue|github_pr)\s+number="([^"]+)"(?:\s+title="([^"]*)")?(?:\s+url="([^"]*)")?\s*\/>|<error_context\s+label="([^"]*)">[\s\S]*?<\/error_context>|<folder\s+path="([^"]+)"\s*\/>/g;
 const MENTION_TAG_TEST =
   /<(?:file\s+path|folder\s+path|github_issue\s+number|github_pr\s+number|error_context\s+label)="[^"]+"/;
-const SLASH_COMMAND_START = /^\/([a-zA-Z][\w-]*)(?=\s|$)/;
+// Matches every slash command in the string, at the start or after whitespace —
+// not just the leading one. Submitted prompts have their <skill /> tags flattened
+// to plain /name text, so a prompt using several skills arrives here as multiple
+// /name tokens that each need a chip.
+const SLASH_COMMAND_REGEX = /(^|\s)\/([a-zA-Z][\w-]*)(?=\s|$)/g;
+const SLASH_COMMAND_TEST = /(?:^|\s)\/[a-zA-Z][\w-]*(?=\s|$)/;
 
 const inlineComponents: Components = {
   ...baseComponents,
@@ -42,7 +47,7 @@ export const InlineMarkdown = memo(function InlineMarkdown({
 });
 
 export function hasMentionTags(content: string): boolean {
-  return MENTION_TAG_TEST.test(content) || SLASH_COMMAND_START.test(content);
+  return MENTION_TAG_TEST.test(content) || SLASH_COMMAND_TEST.test(content);
 }
 
 export const hasFileMentions = hasMentionTags;
@@ -88,30 +93,36 @@ export function MentionChip({
   );
 }
 
-export function parseMentionTags(content: string): ReactNode[] {
-  const parts: ReactNode[] = [];
-  let lastIndex = 0;
+interface MentionMatch {
+  start: number;
+  end: number;
+  node: ReactNode;
+}
 
-  const slashMatch = content.match(SLASH_COMMAND_START);
-  if (slashMatch) {
-    parts.push(
-      <MentionChip key="slash-cmd" icon={null} label={`/${slashMatch[1]}`} />,
-    );
-    lastIndex = slashMatch[0].length;
+function collectMentionMatches(content: string): MentionMatch[] {
+  const matches: MentionMatch[] = [];
+
+  for (const match of content.matchAll(SLASH_COMMAND_REGEX)) {
+    // Group 1 is the leading start-of-string/whitespace boundary; keep it as
+    // surrounding text so only the /command itself becomes a chip.
+    const leading = match[1] ?? "";
+    const start = (match.index ?? 0) + leading.length;
+    matches.push({
+      start,
+      end: start + match[0].length - leading.length,
+      node: (
+        <MentionChip
+          key={`slash-${start}`}
+          icon={null}
+          label={`/${match[2]}`}
+        />
+      ),
+    });
   }
 
   for (const match of content.matchAll(MENTION_TAG_REGEX)) {
     const matchIndex = match.index ?? 0;
-    if (matchIndex < lastIndex) continue;
-
-    if (matchIndex > lastIndex) {
-      parts.push(
-        <InlineMarkdown
-          key={`text-${lastIndex}`}
-          content={content.slice(lastIndex, matchIndex)}
-        />,
-      );
-    }
+    let node: ReactNode = null;
 
     if (match[1]) {
       const filePath = unescapeXmlAttr(match[1]);
@@ -119,12 +130,12 @@ export function parseMentionTags(content: string): ReactNode[] {
       const fileName = segments.pop() ?? filePath;
       const parentDir = segments.pop();
       const label = parentDir ? `${parentDir}/${fileName}` : fileName;
-      parts.push(
+      node = (
         <MentionChip
           key={`file-${matchIndex}`}
           icon={<File size={12} />}
           label={label}
-        />,
+        />
       );
     } else if (match[2]) {
       const kind = match[2] === "github_pr" ? "pr" : "issue";
@@ -134,37 +145,66 @@ export function parseMentionTags(content: string): ReactNode[] {
       const label = issueTitle
         ? `#${issueNumber} - ${issueTitle}`
         : `#${issueNumber}`;
-      parts.push(
+      node = (
         <GithubRefChip
           key={`${match[2]}-${matchIndex}`}
           href={issueUrl}
           kind={kind}
         >
           {label}
-        </GithubRefChip>,
+        </GithubRefChip>
       );
     } else if (match[6]) {
-      parts.push(
+      node = (
         <MentionChip
           key={`error-ctx-${matchIndex}`}
           icon={<Warning size={12} />}
           label={unescapeXmlAttr(match[6])}
-        />,
+        />
       );
     } else if (match[7]) {
       const folderPath = unescapeXmlAttr(match[7]);
       const segments = folderPath.split("/").filter(Boolean);
       const folderName = segments.pop() ?? folderPath;
-      parts.push(
+      node = (
         <MentionChip
           key={`folder-${matchIndex}`}
           icon={<Folder size={12} />}
           label={folderName}
+        />
+      );
+    }
+
+    if (node) {
+      matches.push({
+        start: matchIndex,
+        end: matchIndex + match[0].length,
+        node,
+      });
+    }
+  }
+
+  return matches.sort((a, b) => a.start - b.start);
+}
+
+export function parseMentionTags(content: string): ReactNode[] {
+  const parts: ReactNode[] = [];
+  let lastIndex = 0;
+
+  for (const { start, end, node } of collectMentionMatches(content)) {
+    if (start < lastIndex) continue;
+
+    if (start > lastIndex) {
+      parts.push(
+        <InlineMarkdown
+          key={`text-${lastIndex}`}
+          content={content.slice(lastIndex, start)}
         />,
       );
     }
 
-    lastIndex = matchIndex + match[0].length;
+    parts.push(node);
+    lastIndex = end;
   }
 
   if (lastIndex < content.length) {