diff --git a/apps/web/src/components/ChatMarkdown.tsx b/apps/web/src/components/ChatMarkdown.tsx
index 1d8920e4812..711a545d90a 100644
--- a/apps/web/src/components/ChatMarkdown.tsx
+++ b/apps/web/src/components/ChatMarkdown.tsx
@@ -120,6 +120,20 @@ const EMPTY_MARKDOWN_SKILLS: ReadonlyArray<Pick<ServerProviderSkill, "name" | "d
 const CODE_FENCE_LANGUAGE_REGEX = /(?:^|\s)language-([^\s]+)/;
 const MAX_HIGHLIGHT_CACHE_ENTRIES = 500;
 const MAX_HIGHLIGHT_CACHE_MEMORY_BYTES = 50 * 1024 * 1024;
+
+interface MarkdownActionFailureContext {
+  readonly operation: string;
+  readonly target?: string;
+  readonly format?: "markdown" | "csv";
+  readonly language?: string;
+  readonly fenceTitle?: string;
+  readonly copyTarget?: string;
+}
+
+function reportMarkdownActionFailure(context: MarkdownActionFailureContext, cause: unknown): void {
+  console.error("[chat-markdown] action failed", context, cause);
+}
+
 const highlightedCodeCache = new LRUCache<string>(
   MAX_HIGHLIGHT_CACHE_ENTRIES,
   MAX_HIGHLIGHT_CACHE_MEMORY_BYTES,
@@ -332,7 +346,9 @@ function MarkdownTable({ children, ...props }: React.ComponentProps<"table">) {
           copiedTimerRef.current = null;
         }, 1200);
       })
-      .catch(() => undefined);
+      .catch((cause) => {
+        reportMarkdownActionFailure({ operation: "copy-table", format }, cause);
+      });
   }, []);
 
   useEffect(
@@ -529,8 +545,17 @@ function MarkdownCodeBlock({
           copiedTimerRef.current = null;
         }, 1200);
       })
-      .catch(() => undefined);
-  }, [code]);
+      .catch((cause) => {
+        reportMarkdownActionFailure(
+          {
+            operation: "copy-code-block",
+            language,
+            ...(fenceTitle ? { fenceTitle } : {}),
+          },
+          cause,
+        );
+      });
+  }, [code, fenceTitle, language]);
 
   useEffect(
     () => () => {
@@ -977,18 +1002,36 @@ const MarkdownFileLink = memo(function MarkdownFileLink({
 }: MarkdownFileLinkProps) {
   const handleOpenInEditor = useCallback(() => {
     void (async () => {
-      const result = await onOpen(targetPath);
-      if (result._tag === "Success" || isAtomCommandInterrupted(result)) {
-        return;
+      try {
+        const result = await onOpen(targetPath);
+        if (result._tag === "Success" || isAtomCommandInterrupted(result)) {
+          return;
+        }
+        reportMarkdownActionFailure(
+          { operation: "open-file-in-editor", target: targetPath },
+          result.cause,
+        );
+        const error = squashAtomCommandFailure(result);
+        toastManager.add(
+          stackedThreadToast({
+            type: "error",
+            title: "Unable to open file",
+            description: error instanceof Error ? error.message : "An error occurred.",
+          }),
+        );
+      } catch (cause) {
+        reportMarkdownActionFailure(
+          { operation: "open-file-in-editor", target: targetPath },
+          cause,
+        );
+        toastManager.add(
+          stackedThreadToast({
+            type: "error",
+            title: "Unable to open file",
+            description: cause instanceof Error ? cause.message : "An error occurred.",
+          }),
+        );
       }
-      const error = squashAtomCommandFailure(result);
-      toastManager.add(
-        stackedThreadToast({
-          type: "error",
-          title: "Unable to open file",
-          description: error instanceof Error ? error.message : "An error occurred.",
-        }),
-      );
     })();
   }, [onOpen, targetPath]);
 
@@ -1005,52 +1048,77 @@ const MarkdownFileLink = memo(function MarkdownFileLink({
       return;
     }
     void (async () => {
-      const result = await onOpenInBrowser();
-      if (result._tag === "Success" || isAtomCommandInterrupted(result)) {
-        return;
+      try {
+        const result = await onOpenInBrowser();
+        if (result._tag === "Success" || isAtomCommandInterrupted(result)) {
+          return;
+        }
+        reportMarkdownActionFailure(
+          { operation: "open-file-in-browser", target: targetPath },
+          result.cause,
+        );
+        const error = squashAtomCommandFailure(result);
+        toastManager.add(
+          stackedThreadToast({
+            type: "error",
+            title: "Unable to open file in browser",
+            description: error instanceof Error ? error.message : "An error occurred.",
+          }),
+        );
+      } catch (cause) {
+        reportMarkdownActionFailure(
+          { operation: "open-file-in-browser", target: targetPath },
+          cause,
+        );
+        toastManager.add(
+          stackedThreadToast({
+            type: "error",
+            title: "Unable to open file in browser",
+            description: cause instanceof Error ? cause.message : "An error occurred.",
+          }),
+        );
       }
-      const error = squashAtomCommandFailure(result);
-      toastManager.add(
-        stackedThreadToast({
-          type: "error",
-          title: "Unable to open file in browser",
-          description: error instanceof Error ? error.message : "An error occurred.",
-        }),
-      );
     })();
-  }, [onOpenInBrowser]);
-
-  const handleCopy = useCallback((value: string, title: string) => {
-    if (typeof window === "undefined" || !navigator.clipboard?.writeText) {
-      toastManager.add(
-        stackedThreadToast({
-          type: "error",
-          title: `Failed to copy ${title.toLowerCase()}`,
-          description: "Clipboard API unavailable.",
-        }),
-      );
-      return;
-    }
+  }, [onOpenInBrowser, targetPath]);
 
-    void navigator.clipboard.writeText(value).then(
-      () => {
-        toastManager.add({
-          type: "success",
-          title: `${title} copied`,
-          description: value,
-        });
-      },
-      (error) => {
+  const handleCopy = useCallback(
+    (value: string, title: string) => {
+      if (typeof window === "undefined" || !navigator.clipboard?.writeText) {
         toastManager.add(
           stackedThreadToast({
             type: "error",
             title: `Failed to copy ${title.toLowerCase()}`,
-            description: error instanceof Error ? error.message : "An error occurred.",
+            description: "Clipboard API unavailable.",
           }),
         );
-      },
-    );
-  }, []);
+        return;
+      }
+
+      void navigator.clipboard.writeText(value).then(
+        () => {
+          toastManager.add({
+            type: "success",
+            title: `${title} copied`,
+            description: value,
+          });
+        },
+        (error) => {
+          reportMarkdownActionFailure(
+            { operation: "copy-file-path", target: targetPath, copyTarget: title },
+            error,
+          );
+          toastManager.add(
+            stackedThreadToast({
+              type: "error",
+              title: `Failed to copy ${title.toLowerCase()}`,
+              description: error instanceof Error ? error.message : "An error occurred.",
+            }),
+          );
+        },
+      );
+    },
+    [targetPath],
+  );
 
   const handleContextMenu = useCallback(
     async (event: ReactMouseEvent<HTMLAnchorElement>) => {
@@ -1060,32 +1128,39 @@ const MarkdownFileLink = memo(function MarkdownFileLink({
       const api = readLocalApi();
       if (!api) return;
 
-      const clicked = await api.contextMenu.show(
-        [
-          { id: "open", label: "Open in editor" },
-          ...(onOpenInBrowser
-            ? ([{ id: "open-in-browser", label: "Open in integrated browser" }] as const)
-            : []),
-          { id: "copy-relative", label: "Copy relative path" },
-          { id: "copy-full", label: "Copy full path" },
-        ] as const,
-        { x: event.clientX, y: event.clientY },
-      );
+      try {
+        const clicked = await api.contextMenu.show(
+          [
+            { id: "open", label: "Open in editor" },
+            ...(onOpenInBrowser
+              ? ([{ id: "open-in-browser", label: "Open in integrated browser" }] as const)
+              : []),
+            { id: "copy-relative", label: "Copy relative path" },
+            { id: "copy-full", label: "Copy full path" },
+          ] as const,
+          { x: event.clientX, y: event.clientY },
+        );
 
-      if (clicked === "open") {
-        handleOpenInEditor();
-        return;
-      }
-      if (clicked === "open-in-browser") {
-        handleOpenInBrowser();
-        return;
-      }
-      if (clicked === "copy-relative") {
-        handleCopy(displayPath, "Relative path");
-        return;
-      }
-      if (clicked === "copy-full") {
-        handleCopy(targetPath, "Full path");
+        if (clicked === "open") {
+          handleOpenInEditor();
+          return;
+        }
+        if (clicked === "open-in-browser") {
+          handleOpenInBrowser();
+          return;
+        }
+        if (clicked === "copy-relative") {
+          handleCopy(displayPath, "Relative path");
+          return;
+        }
+        if (clicked === "copy-full") {
+          handleCopy(targetPath, "Full path");
+        }
+      } catch (cause) {
+        reportMarkdownActionFailure(
+          { operation: "show-file-context-menu", target: targetPath },
+          cause,
+        );
       }
     },
     [displayPath, handleCopy, handleOpenInBrowser, handleOpenInEditor, onOpenInBrowser, targetPath],
@@ -1315,22 +1390,32 @@ function ChatMarkdown({
                 event.stopPropagation();
                 const api = readLocalApi();
                 if (!api) return;
-                void api.contextMenu
-                  .show(
-                    [
-                      { id: "open-in-browser", label: "Open in integrated browser" },
-                      { id: "open-external", label: "Open in system browser" },
-                    ] as const,
-                    { x: event.clientX, y: event.clientY },
-                  )
-                  .then((clicked) => {
+                void (async () => {
+                  let operation = "show-link-context-menu";
+                  try {
+                    const clicked = await api.contextMenu.show(
+                      [
+                        { id: "open-in-browser", label: "Open in integrated browser" },
+                        { id: "open-external", label: "Open in system browser" },
+                      ] as const,
+                      { x: event.clientX, y: event.clientY },
+                    );
                     if (clicked === "open-in-browser") {
-                      void openExternalLinkInPreview(href);
+                      operation = "open-link-in-preview";
+                      const result = await openExternalLinkInPreview(href);
+                      if (result._tag === "Failure" && !isAtomCommandInterrupted(result)) {
+                        reportMarkdownActionFailure({ operation, target: href }, result.cause);
+                      }
                       return;
                     }
-                    if (clicked === "open-external") return api.shell.openExternal(href);
-                  })
-                  .catch(() => undefined);
+                    if (clicked === "open-external") {
+                      operation = "open-link-external";
+                      await api.shell.openExternal(href);
+                    }
+                  } catch (cause) {
+                    reportMarkdownActionFailure({ operation, target: href }, cause);
+                  }
+                })();
               }}
             >
               {faviconHost ? (