diff --git a/src/renderer/src/view_models/FacebookViewModel/jobs_delete.test.ts b/src/renderer/src/view_models/FacebookViewModel/jobs_delete.test.ts
index bfd8241f..e59097d4 100644
--- a/src/renderer/src/view_models/FacebookViewModel/jobs_delete.test.ts
+++ b/src/renderer/src/view_models/FacebookViewModel/jobs_delete.test.ts
@@ -121,6 +121,24 @@ function mockSafeExecuteJavaScript(
           return { success: true, value: false };
         case "countSelectableItems":
           return { success: true, value: itemsPerBatch };
+        case "describeBlockingUI":
+          // A password confirmation modal over the activity log
+          return {
+            success: true,
+            value: {
+              url: "https://www.facebook.com/123/allactivity",
+              passwordInputCount: 1,
+              passwordInputs: [{ name: "pass", ariaLabel: "Password" }],
+              dialogs: [
+                {
+                  ariaLabel: "Confirm password",
+                  hasPasswordInput: true,
+                  buttons: ["Continue"],
+                  text: "Please re-enter your password",
+                },
+              ],
+            },
+          };
         case "clickDeletePostsOption":
           return { success: true, value: clickTrashSuccess };
         case "confirmDeletion":
@@ -280,5 +298,62 @@ describe("FacebookViewModel Delete Jobs", () => {
       // The job errored before completing, so it is never marked finished
       expect(vm.progress.isDeleteActivityFinished).toBe(false);
     });
+
+    it("never captures a password", () => {
+      const PASSWORD = "correct-horse-battery-staple";
+
+      document.title = "Facebook";
+      document.body.innerHTML = `
+        <div role="dialog" aria-modal="true" aria-label="Confirm password">
+          <h2><span>Please re-enter your password</span></h2>
+          <form>
+            <input type="password" name="pass" aria-label="Password" placeholder="Password" />
+            <div role="button" aria-label="Continue"><span>Continue</span></div>
+          </form>
+        </div>
+      `;
+
+      const input = document.querySelector(
+        'input[type="password"]',
+      ) as HTMLInputElement;
+      // As a user types it, and as a page could reflect it into the markup
+      input.value = PASSWORD;
+      input.setAttribute("value", PASSWORD);
+
+      const snapshot = eval(DeleteJobs.BLOCKING_UI_JS);
+
+      expect(JSON.stringify(snapshot)).not.toContain(PASSWORD);
+      // Still captures what we need to write a selector
+      expect(snapshot.passwordInputs[0]).toMatchObject({
+        name: "pass",
+        ariaLabel: "Password",
+      });
+      expect(snapshot.dialogs[0].buttons).toContain("Continue");
+
+      document.body.innerHTML = "";
+    });
+
+    it("attaches a description of whatever blocked us to the error report", async () => {
+      const vm = createMockFacebookViewModel({
+        facebookAccount: createMockFacebookAccount({ deleteWallPosts: true }),
+      });
+      mockSafeExecuteJavaScript(vm, {
+        batchesPerCategory: 1,
+        clickTrashSuccess: false,
+      });
+
+      await DeleteJobs.runJobDeleteActivity(vm, 3);
+
+      const sensitiveContext = vi.mocked(vm.error).mock.calls[0][2];
+      expect(sensitiveContext.blockingUI).toMatchObject({
+        passwordInputCount: 1,
+        dialogs: [
+          expect.objectContaining({
+            ariaLabel: "Confirm password",
+            hasPasswordInput: true,
+          }),
+        ],
+      });
+    });
   });
 });
diff --git a/src/renderer/src/view_models/FacebookViewModel/jobs_delete.ts b/src/renderer/src/view_models/FacebookViewModel/jobs_delete.ts
index f6a5c477..f745104c 100644
--- a/src/renderer/src/view_models/FacebookViewModel/jobs_delete.ts
+++ b/src/renderer/src/view_models/FacebookViewModel/jobs_delete.ts
@@ -16,14 +16,71 @@ const BATCH_COOLDOWN_MS = 5000;
 const PROCESSING_BACKOFF_MS = 60000;
 const MAX_PROCESSING_RETRIES = 15;
 
+/**
+ * Attributes and rendered text only: never `.value` (so we don't capture a password)
+ * Exported so the tests can run the shipping code against this
+ */
+export const BLOCKING_UI_JS = `(() => {
+  const text = (el) => ((el.innerText || el.textContent) || '').replace(/\\s+/g, ' ').trim();
+  const attr = (el, name) => (el.getAttribute ? el.getAttribute(name) : null);
+
+  return {
+    url: document.location ? document.location.href.split('?')[0] : '',
+    title: (document.title || '').slice(0, 120),
+    bodyText: text(document.body).slice(0, 500),
+    passwordInputCount: document.querySelectorAll('input[type="password"]').length,
+    passwordInputs: Array.from(document.querySelectorAll('input[type="password"]'))
+      .slice(0, 3)
+      .map((input) => ({
+        name: attr(input, 'name'),
+        id: attr(input, 'id'),
+        ariaLabel: attr(input, 'aria-label'),
+        placeholder: attr(input, 'placeholder'),
+        autocomplete: attr(input, 'autocomplete'),
+      })),
+    dialogs: Array.from(document.querySelectorAll('div[role="dialog"]'))
+      .slice(0, 5)
+      .map((dialog) => ({
+        ariaLabel: attr(dialog, 'aria-label'),
+        ariaModal: attr(dialog, 'aria-modal'),
+        hasPasswordInput: dialog.querySelector('input[type="password"]') !== null,
+        buttons: Array.from(dialog.querySelectorAll('div[role="button"], button'))
+          .slice(0, 8)
+          .map((button) => (attr(button, 'aria-label') || text(button)).slice(0, 40))
+          .filter((label) => label.length > 0),
+        text: text(dialog).slice(0, 300),
+      })),
+  };
+})()`;
+
+/**
+ * Describe whatever Facebook has put on screen, so an error report identifies the modal
+ * that blocked us such as a password confirmation
+ */
+async function describeBlockingUI(
+  vm: FacebookViewModel,
+): Promise<Record<string, unknown>> {
+  const result = await vm.safeExecuteJavaScript<Record<string, unknown>>(
+    BLOCKING_UI_JS,
+    "describeBlockingUI",
+  );
+  return result.success
+    ? result.value
+    : { error: `Could not inspect the page: ${result.error}` };
+}
+
 async function reportDeleteWallPostsError(
   vm: FacebookViewModel,
   jobIndex: number,
   errorType: AutomationErrorType,
   errorReportData: Record<string, unknown>,
 ) {
+  const blockingUI = await describeBlockingUI(vm);
+  vm.log("reportDeleteWallPostsError", { errorType, blockingUI });
+
   await vm.error(errorType, errorReportData, {
     currentURL: vm.webview?.getURL(),
+    blockingUI,
   });
   await Helpers.errorJob(vm, jobIndex);
 }
@@ -305,10 +362,11 @@ async function deleteCategory(
     // Select all currently loaded items
     const toggled = await toggleSelectAllCheckbox(vm, true);
     if (!toggled) {
-      vm.log(
-        "deleteCategory",
-        `Could not select items for category ${category.setting}`,
-      );
+      // Exits without an error report, so log the page
+      vm.log("deleteCategory", {
+        message: `Could not select items for category ${category.setting}`,
+        blockingUI: await describeBlockingUI(vm),
+      });
       break;
     }