diff --git a/test/e2e/support/selectors.js b/test/e2e/support/selectors.js
index d68f2d8fe..4bbc5acf4 100644
--- a/test/e2e/support/selectors.js
+++ b/test/e2e/support/selectors.js
@@ -8,87 +8,86 @@
 
 // publisherWebview
 // Purpose: Resolve the Publisher extension's nested iframe and return its inner body.
-// - Retries, reloads once, and verifies content presence for robustness.
+// - Uses waitUntil for cleaner retry logic, reloads once if needed.
 // When to use: Before any .findByTestId() inside the extension.
 Cypress.Commands.add("publisherWebview", () => {
-  // Wait up to 60 seconds (30 retries x 2s) for the publisher iframe, then reload once and try 10 more times.
-  // If still not found, log a clear error and fail the test.
-  function findPublisherIframe(retries = 30, hasReloaded = false) {
-    return cy
-      .get("iframe.webview.ready", { timeout: 30000 })
-      .then(($iframes) => {
-        if (Cypress.env("DEBUG_CYPRESS") === "true") {
-          cy.task("print", `Found ${$iframes.length} webview.ready iframes`);
-        }
-        const $target = Cypress.$($iframes).filter((i, el) =>
-          (el.src || "").includes("extensionId=posit.publisher"),
-        );
-        if (Cypress.env("DEBUG_CYPRESS") === "true") {
-          cy.task("print", `Found ${$target.length} publisher iframes`);
-        }
-        if ($target.length > 0) {
-          expect(
-            $target.length,
-            "publisher webview iframe present",
-          ).to.be.greaterThan(0);
-
-          // Verify iframe has actual content
-          const body = $target[0].contentDocument?.body;
-          if (body) {
-            const bodyText = body.innerText || "";
-            const hasAutomationElements =
-              body.querySelector("[data-automation]") !== null;
-
-            if (bodyText.includes("Posit") || hasAutomationElements) {
-              cy.log(
-                "Publisher iframe content verified to contain expected content",
-              );
-            } else {
-              cy.log(
-                "WARNING: Publisher iframe found but content may not be fully loaded",
-              );
-              cy.log(`Content sample: ${bodyText.substring(0, 100)}`);
-            }
-          }
+  let hasReloaded = false;
 
-          return cy.wrap($target[0].contentDocument.body);
-        } else if (retries > 0) {
-          // eslint-disable-next-line cypress/no-unnecessary-waiting
-          return cy
-            .wait(2000)
-            .then(() => findPublisherIframe(retries - 1, hasReloaded));
-        } else if (!hasReloaded) {
-          cy.log("Publisher iframe not found after retries, reloading page...");
-          return cy.reload().then(() => findPublisherIframe(10, true));
-        } else {
-          cy.log(
-            "ERROR: Publisher iframe not found after waiting and reloading. UI may not have loaded correctly. If this happens often, check Connect service health or add a backend health check before running tests.",
-          );
-          cy.log("Attempting extreme iframe finder as last resort...");
-          // Try extreme finder as absolute last resort
-          return cy.findPublisherIframeExtreme().then(($iframe) => {
-            const iframe = $iframe[0];
-            if (
-              iframe &&
-              iframe.contentDocument &&
-              iframe.contentDocument.body
-            ) {
-              return cy.wrap(iframe.contentDocument.body);
-            } else {
-              throw new Error(
-                "Even extreme iframe finder failed - iframe content not accessible",
-              );
-            }
-          });
+  // Helper to find the publisher iframe and return its body
+  const findPublisherIframeBody = () => {
+    return cy.get("body").then(($body) => {
+      const $iframes = $body.find("iframe.webview.ready");
+      if (Cypress.env("DEBUG_CYPRESS") === "true") {
+        cy.task("print", `Found ${$iframes.length} webview.ready iframes`);
+      }
+
+      // Filter to find the publisher iframe using JavaScript (not CSS selector)
+      // because the src URL contains encoded characters
+      const $target = $iframes.filter((i, el) =>
+        (el.src || "").includes("extensionId=posit.publisher"),
+      );
+
+      if ($target.length > 0) {
+        const outerBody = $target[0].contentDocument?.body;
+        if (outerBody) {
+          const bodyText = outerBody.innerText || "";
+          const hasAutomationElements =
+            outerBody.querySelector("[data-automation]") !== null;
+
+          if (bodyText.includes("Posit") || hasAutomationElements) {
+            cy.log("Publisher iframe content verified");
+            return outerBody;
+          }
         }
-      });
-  }
-  return findPublisherIframe()
-    .should("not.be.empty")
-    .then(cy.wrap)
-    .find("iframe#active-frame", { timeout: 30000 })
-    .its("0.contentDocument.body")
-    .should("not.be.empty")
+      }
+      return null;
+    });
+  };
+
+  // Wait for publisher iframe using cypress-wait-until
+  return cy
+    .waitUntil(
+      () =>
+        findPublisherIframeBody().then((body) => {
+          if (body) return body;
+
+          // If not found and haven't reloaded yet, log it
+          if (!hasReloaded) {
+            cy.log(
+              "Publisher iframe not found, will reload page on next attempt...",
+            );
+          }
+          return false;
+        }),
+      {
+        timeout: 60000,
+        interval: 2000,
+        errorMsg:
+          "Publisher iframe not found. UI may not have loaded correctly.",
+      },
+    )
+    .then((outerBody) => {
+      // If still not found after timeout, try reload once
+      if (!outerBody && !hasReloaded) {
+        hasReloaded = true;
+        cy.log("Reloading page to find publisher iframe...");
+        cy.reload();
+        return cy.waitUntil(() => findPublisherIframeBody(), {
+          timeout: 20000,
+          interval: 2000,
+          errorMsg: "Publisher iframe not found even after page reload.",
+        });
+      }
+      return outerBody;
+    })
+    .then((outerBody) => {
+      // Now find the inner active-frame iframe
+      return cy
+        .wrap(outerBody)
+        .find("iframe#active-frame", { timeout: 30000 })
+        .its("0.contentDocument.body")
+        .should("not.be.empty");
+    })
     .then((body) => {
       // We need to wrap in jQuery to use html() and text()
       const $body = Cypress.$(body);
@@ -160,101 +159,49 @@ Cypress.Commands.add("publisherWebviewExtreme", () => {
 // and ensure the UI is stable before clicking.
 // When to use: Before opening the Publisher webview from VS Code UI.
 Cypress.Commands.add("getPublisherSidebarIcon", () => {
-  // Advanced Publisher icon finder that waits for extension stability
-  const maxAttempts = 30;
-  const stabilityChecks = 3; // Number of consecutive checks to confirm stability
-
-  function waitForExtensionStability(attempt = 1) {
-    cy.log(`Checking extension stability (attempt ${attempt}/${maxAttempts})`);
-
-    return cy.get("body").then(($body) => {
-      const bodyText = $body.text();
-      const isLoading =
-        bodyText.includes("starting posit publisher") ||
-        bodyText.includes("python extension loading") ||
-        bodyText.includes("please wait") ||
-        bodyText.includes("activating extension");
-
-      if (isLoading) {
-        cy.log("Extension still loading, waiting for stability...");
-        if (attempt < maxAttempts) {
-          // eslint-disable-next-line cypress/no-unnecessary-waiting
-          cy.wait(1500);
-          return waitForExtensionStability(attempt + 1);
-        }
-        cy.log(
-          "WARNING: Extension still appears to be loading after max attempts",
+  const selectors = [
+    'button[aria-label*="Posit Publisher"]',
+    'button[title*="Posit Publisher"]',
+    'button[aria-label*="Publisher"]',
+    'button[title*="Publisher"]',
+    ".codicon-posit-publisher-publish",
+  ];
+
+  const loadingIndicators = [
+    "starting posit publisher",
+    "python extension loading",
+    "please wait",
+    "activating extension",
+  ];
+
+  // Wait for extension loading indicators to clear using cypress-wait-until
+  cy.waitUntil(
+    () =>
+      cy.get("body").then(($body) => {
+        const bodyText = $body.text().toLowerCase();
+        const isLoading = loadingIndicators.some((indicator) =>
+          bodyText.includes(indicator),
         );
-      } else {
-        cy.log("Extension loading indicators cleared");
-      }
-
-      return findAndVerifyIcon();
-    });
-  }
-
-  function findAndVerifyIcon() {
-    const selectors = [
-      'button[aria-label*="Posit Publisher"]',
-      'button[title*="Posit Publisher"]',
-      'button[aria-label*="Publisher"]',
-      'button[title*="Publisher"]',
-      ".codicon-posit-publisher-publish",
-    ];
-
-    function trySelectors(selectorIndex = 0, stabilityCount = 0) {
-      if (selectorIndex >= selectors.length) {
-        cy.log("No icon found with any selector, retrying...");
-        // eslint-disable-next-line cypress/no-unnecessary-waiting
-        cy.wait(2000);
-        return findAndVerifyIcon();
-      }
-
-      const selector = selectors[selectorIndex];
-      cy.log(`Trying selector: ${selector}`);
-
-      return cy.get("body").then(($body) => {
-        const elements = $body.find(selector);
-
-        if (elements.length > 0 && elements.is(":visible")) {
-          cy.log(`Found potentially stable icon with ${selector}`);
-
-          // Wait and verify stability multiple times
-          // eslint-disable-next-line cypress/no-unnecessary-waiting
-          return cy.wait(1000).then(() => {
-            return cy.get("body").then(($bodyAfter) => {
-              const elementsAfter = $bodyAfter.find(selector);
-
-              if (elementsAfter.length > 0 && elementsAfter.is(":visible")) {
-                if (stabilityCount >= stabilityChecks - 1) {
-                  cy.log(
-                    `Icon confirmed stable after ${stabilityChecks} checks`,
-                  );
-                  return cy.get(selector).first().should("be.visible");
-                } else {
-                  cy.log(
-                    `Stability check ${stabilityCount + 1}/${stabilityChecks} passed`,
-                  );
-                  return trySelectors(selectorIndex, stabilityCount + 1);
-                }
-              } else {
-                cy.log(
-                  "Icon disappeared during stability check, trying next selector",
-                );
-                return trySelectors(selectorIndex + 1, 0);
-              }
-            });
-          });
-        } else {
-          return trySelectors(selectorIndex + 1, 0);
+        if (isLoading) {
+          cy.log("Extension still loading, waiting...");
         }
-      });
-    }
+        return !isLoading;
+      }),
+    {
+      timeout: 45000,
+      interval: 1500,
+      errorMsg: "Extension loading indicators did not clear in time",
+    },
+  );
 
-    return trySelectors();
-  }
+  // Build a combined selector to find the icon with any of the patterns
+  const combinedSelector = selectors.join(", ");
 
-  return waitForExtensionStability().should("be.visible");
+  // Use Cypress's built-in retry to find and verify the icon is visible
+  return cy
+    .get(combinedSelector, { timeout: 30000 })
+    .first()
+    .should("be.visible");
 });
 
 // toggleCredentialsSection / refreshCredentials / toggleHelpSection
diff --git a/test/e2e/support/sequences.js b/test/e2e/support/sequences.js
index 0c16db06e..1d07b0a91 100644
--- a/test/e2e/support/sequences.js
+++ b/test/e2e/support/sequences.js
@@ -323,9 +323,7 @@ Cypress.Commands.add(
             const isChecked = $checkbox.prop("checked");
             if (!isChecked) {
               cy.wrap($checkbox).click({ force: true });
-              // eslint-disable-next-line cypress/no-unnecessary-waiting
-              cy.wait(500); // Small wait after click
-              // Verify the click worked
+              // Verify the click worked - Cypress will retry until checked
               cy.wrap($checkbox).should("be.checked");
             }
           });
@@ -473,44 +471,42 @@ Cypress.Commands.add("startCredentialCreationFlow", (platform = "server") => {
   cy.waitForPublisherIframe();
   cy.debugIframes();
 
-  // Ensure the Credentials section is expanded (visibility-based check with retry)
-  const ensureCredentialsSectionExpanded = (attempt = 0) => {
-    if (attempt > 3) {
-      cy.log("Max attempts reached ensuring credentials section expansion");
-      return;
-    }
-    cy.publisherWebview()
-      .findByTestId("publisher-credentials-section")
-      .then(($section) => {
-        const $sec = Cypress.$($section);
-        const isVisibleEmpty =
-          $sec
-            .find(':contains("No credentials have been added yet.")')
-            .filter(":visible").length > 0;
-        const hasVisibleBody =
-          $sec.find(".pane-body:visible").length > 0 ||
-          $sec.find(".tree:visible").length > 0;
-
-        const expanded = isVisibleEmpty || hasVisibleBody;
-
-        if (!expanded) {
-          cy.log(
-            `Credentials section appears collapsed, expanding (attempt ${
-              attempt + 1
-            })`,
-          );
-          $sec.find(".title").trigger("click");
-          // eslint-disable-next-line cypress/no-unnecessary-waiting
-          cy.wait(200).then(() =>
-            ensureCredentialsSectionExpanded(attempt + 1),
-          );
-        } else {
-          cy.log("Credentials section expanded");
-        }
-      });
-  };
+  // Ensure the Credentials section is expanded using Cypress retry assertions
+  cy.publisherWebview()
+    .findByTestId("publisher-credentials-section")
+    .then(($section) => {
+      const $sec = Cypress.$($section);
+      const isVisibleEmpty =
+        $sec
+          .find(':contains("No credentials have been added yet.")')
+          .filter(":visible").length > 0;
+      const hasVisibleBody =
+        $sec.find(".pane-body:visible").length > 0 ||
+        $sec.find(".tree:visible").length > 0;
+
+      const expanded = isVisibleEmpty || hasVisibleBody;
+
+      if (!expanded) {
+        cy.log("Credentials section appears collapsed, expanding");
+        $sec.find(".title").trigger("click");
+      }
+    });
 
-  ensureCredentialsSectionExpanded();
+  // Wait for section to be expanded by asserting content is visible
+  cy.publisherWebview()
+    .findByTestId("publisher-credentials-section")
+    .should(($section) => {
+      const $sec = Cypress.$($section);
+      const isVisibleEmpty =
+        $sec
+          .find(':contains("No credentials have been added yet.")')
+          .filter(":visible").length > 0;
+      const hasVisibleBody =
+        $sec.find(".pane-body:visible").length > 0 ||
+        $sec.find(".tree:visible").length > 0;
+      expect(isVisibleEmpty || hasVisibleBody, "Credentials section expanded")
+        .to.be.true;
+    });
 
   // After ensuring expansion, proceed
   cy.publisherWebview()
diff --git a/test/e2e/support/workbench.js b/test/e2e/support/workbench.js
index af059c624..80e35125a 100644
--- a/test/e2e/support/workbench.js
+++ b/test/e2e/support/workbench.js
@@ -243,13 +243,13 @@ Cypress.Commands.add("startPositronSession", () => {
 
   // Start a Positron session
   // TODO remove this workaround for "All types of sessions are disabled" error after Workbench 2025.12.0 is released
+  // Wait for network to be idle before clicking to ensure backend is ready
+  cy.waitForNetworkIdle(500);
   cy.get("button")
     .contains("New Session")
     .should("be.visible")
-    .and("be.enabled");
-  // eslint-disable-next-line cypress/no-unnecessary-waiting
-  cy.wait(500);
-  cy.get("button").contains("New Session").click();
+    .and("be.enabled")
+    .click();
   cy.get("button").contains("Positron").click();
   cy.get("button").contains("Launch").click();
 
@@ -401,18 +401,15 @@ Cypress.Commands.add(
     cy.get('.monaco-menu .actions-container[role="menu"]')
       .should("be.visible")
       .within(() => {
-        // Even a double-click the Posit Publisher menu item sometimes fails to open it for some reason
-        // TODO try to determine some other way to make this more reliable than a hardcoded wait
-        // eslint-disable-next-line cypress/no-unnecessary-waiting
-        cy.wait(1_000);
-
-        cy.findByLabelText("Posit Publisher").dblclick();
+        // Wait for the menu item to be fully rendered and actionable before clicking
+        cy.findByLabelText("Posit Publisher")
+          .should("be.visible")
+          .and("not.have.attr", "aria-disabled", "true")
+          .dblclick();
       });
 
-    // Small wait to allow the UI to settle in CI before proceeding
-    // TODO try to determine some other way to make this more reliable than a hardcoded wait
-    // eslint-disable-next-line cypress/no-unnecessary-waiting
-    cy.wait(1_000);
+    // Wait for menu to close before proceeding
+    cy.get('.monaco-menu .actions-container[role="menu"]').should("not.exist");
 
     cy.debugIframes();