diff --git a/src/screenReaderTest.ts b/src/screenReaderTest.ts
index 2c24abd..b8f8229 100644
--- a/src/screenReaderTest.ts
+++ b/src/screenReaderTest.ts
@@ -130,6 +130,91 @@ export interface ScreenReaderPlaywright extends ScreenReader {
   navigateToWebContent(options?: CaptureCommandOptions): Promise<void>;
 }
 
+const closeMenus = async ({
+  screenReaderPlaywright,
+}: {
+  screenReaderPlaywright: ScreenReaderPlaywright;
+}) => {
+  await screenReaderPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Escape },
+    { capture: false },
+  );
+};
+
+const cancelCurrentInteraction = async ({
+  screenReaderPlaywright,
+}: {
+  screenReaderPlaywright: ScreenReaderPlaywright;
+}) => {
+  await screenReaderPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Control },
+    { capture: false },
+  );
+};
+
+const openItemChooser = async ({
+  screenReaderPlaywright,
+}: {
+  screenReaderPlaywright: ScreenReaderPlaywright;
+}) => {
+  let lastSpokenPhrase = "";
+
+  while (!lastSpokenPhrase.toLowerCase().includes("item chooser")) {
+    await cancelCurrentInteraction({ screenReaderPlaywright });
+    await delay(100);
+    await closeMenus({ screenReaderPlaywright });
+    await delay(100);
+
+    await screenReaderPlaywright.perform(
+      voiceOverKeyCodeCommands.openItemChooser,
+      { capture: true },
+    );
+
+    lastSpokenPhrase = await screenReaderPlaywright.lastSpokenPhrase();
+  }
+};
+
+async function selectWebContentItem({
+  screenReaderPlaywright,
+}: {
+  screenReaderPlaywright: ScreenReaderPlaywright;
+}) {
+  // eslint-disable-next-line no-constant-condition
+  while (true) {
+    let matched = false;
+
+    for (const character of "web content") {
+      await cancelCurrentInteraction({ screenReaderPlaywright });
+      await delay(100);
+
+      await screenReaderPlaywright.type(character, { capture: "initial" });
+      const lastSpokenPhrase = await screenReaderPlaywright.lastSpokenPhrase();
+
+      if (lastSpokenPhrase.toLowerCase().includes("web content")) {
+        matched = true;
+
+        break;
+      }
+    }
+
+    if (matched) {
+      break;
+    }
+
+    // Clear the entire Item Chooser search.
+    await screenReaderPlaywright.perform(
+      { keyCode: MacOSKeyCodes.Backspace },
+      { capture: false },
+    );
+    await delay(100);
+  }
+
+  await screenReaderPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Enter },
+    { capture: false },
+  );
+}
+
 const screenReaderPlaywright: ScreenReaderPlaywright =
   screenReader as ScreenReaderPlaywright;
 
@@ -261,14 +346,18 @@ export const screenReaderTest = test.extend<{
         screenReaderPlaywright.navigateToWebContent = async ({
           capture,
         } = {}) => {
+          const currentSpokenPhraseLog = [
+            ...(await screenReaderPlaywright.spokenPhraseLog()),
+          ];
+          const currentItemTextLog = [
+            ...(await screenReaderPlaywright.itemTextLog()),
+          ];
+
           // Ensure application is brought to front and focused.
           await macOSActivate(applicationName);
 
           // Cancel automatic behaviours/previous commands.
-          await screenReaderPlaywright.perform(
-            { keyCode: MacOSKeyCodes.Control },
-            { capture: false },
-          );
+          await cancelCurrentInteraction({ screenReaderPlaywright });
           await delay(100);
 
           // Ensure the document is ready and focused.
@@ -301,31 +390,24 @@ export const screenReaderTest = test.extend<{
               document.body.prepend(marker);
             });
 
-            // Open the web item chooser.
-            await screenReaderPlaywright.perform(
-              voiceOverKeyCodeCommands.openItemChooser,
-              { capture: false },
-            );
-            await delay(500);
-
-            // Filter by "web content" - currently web content items for all browsers
-            // are suffixed by "web content".
-            for (const character of "web content") {
-              await screenReaderPlaywright.type(character, { capture: false });
-              await delay(100);
-            }
-
-            // Select the web content window spot.
-            await screenReaderPlaywright.perform(
-              { keyCode: MacOSKeyCodes.Enter },
-              { capture: false },
-            );
-            await delay(100);
+            // Open item chooser and select web content.
+            await openItemChooser({ screenReaderPlaywright });
+            await selectWebContentItem({ screenReaderPlaywright });
 
             // Navigate into web content.
             await screenReaderPlaywright.interact({ capture: false });
             await delay(100);
 
+            await screenReaderPlaywright.clearSpokenPhraseLog();
+            await screenReaderPlaywright.clearItemTextLog();
+
+            const spokenPhraseLog =
+              await screenReaderPlaywright.spokenPhraseLog();
+            const itemTextLog = await screenReaderPlaywright.itemTextLog();
+
+            spokenPhraseLog.push(...currentSpokenPhraseLog);
+            itemTextLog.push(...currentItemTextLog);
+
             // Navigate to the first element of the page using the provided
             // capture settings.
             await screenReaderPlaywright.next({ capture });
diff --git a/src/voiceOverTest.ts b/src/voiceOverTest.ts
index 727ba95..f8123e5 100644
--- a/src/voiceOverTest.ts
+++ b/src/voiceOverTest.ts
@@ -44,6 +44,91 @@ export interface VoiceOverPlaywright extends VoiceOver {
   ): Promise<void>;
 }
 
+const closeMenus = async ({
+  voiceOverPlaywright,
+}: {
+  voiceOverPlaywright: VoiceOverPlaywright;
+}) => {
+  await voiceOverPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Escape },
+    { capture: false },
+  );
+};
+
+const cancelCurrentInteraction = async ({
+  voiceOverPlaywright,
+}: {
+  voiceOverPlaywright: VoiceOverPlaywright;
+}) => {
+  await voiceOverPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Control },
+    { capture: false },
+  );
+};
+
+const openItemChooser = async ({
+  voiceOverPlaywright,
+}: {
+  voiceOverPlaywright: VoiceOverPlaywright;
+}) => {
+  let lastSpokenPhrase = "";
+
+  while (!lastSpokenPhrase.toLowerCase().includes("item chooser")) {
+    await cancelCurrentInteraction({ voiceOverPlaywright });
+    await delay(100);
+    await closeMenus({ voiceOverPlaywright });
+    await delay(100);
+
+    await voiceOverPlaywright.perform(
+      voiceOverPlaywright.keyboardCommands.openItemChooser,
+      { capture: true },
+    );
+
+    lastSpokenPhrase = await voiceOverPlaywright.lastSpokenPhrase();
+  }
+};
+
+async function selectWebContentItem({
+  voiceOverPlaywright,
+}: {
+  voiceOverPlaywright: VoiceOverPlaywright;
+}) {
+  // eslint-disable-next-line no-constant-condition
+  while (true) {
+    let matched = false;
+
+    for (const character of "web content") {
+      await cancelCurrentInteraction({ voiceOverPlaywright });
+      await delay(100);
+
+      await voiceOverPlaywright.type(character, { capture: "initial" });
+      const lastSpokenPhrase = await voiceOverPlaywright.lastSpokenPhrase();
+
+      if (lastSpokenPhrase.toLowerCase().includes("web content")) {
+        matched = true;
+
+        break;
+      }
+    }
+
+    if (matched) {
+      break;
+    }
+
+    // Clear the entire Item Chooser search.
+    await voiceOverPlaywright.perform(
+      { keyCode: MacOSKeyCodes.Backspace },
+      { capture: false },
+    );
+    await delay(100);
+  }
+
+  await voiceOverPlaywright.perform(
+    { keyCode: MacOSKeyCodes.Enter },
+    { capture: false },
+  );
+}
+
 const voiceOverPlaywright: VoiceOverPlaywright =
   voiceOver as VoiceOverPlaywright;
 
@@ -96,14 +181,18 @@ export const voiceOverTest = test.extend<{
       }
 
       voiceOverPlaywright.navigateToWebContent = async ({ capture } = {}) => {
+        const currentSpokenPhraseLog = [
+          ...(await voiceOverPlaywright.spokenPhraseLog()),
+        ];
+        const currentItemTextLog = [
+          ...(await voiceOverPlaywright.itemTextLog()),
+        ];
+
         // Ensure application is brought to front and focused.
         await macOSActivate(applicationName);
 
         // Cancel automatic behaviours/previous commands.
-        await voiceOverPlaywright.perform(
-          { keyCode: MacOSKeyCodes.Control },
-          { capture: false },
-        );
+        await cancelCurrentInteraction({ voiceOverPlaywright });
         await delay(100);
 
         // Ensure the document is ready and focused.
@@ -136,31 +225,23 @@ export const voiceOverTest = test.extend<{
             document.body.prepend(marker);
           });
 
-          // Open the web item chooser.
-          await voiceOverPlaywright.perform(
-            voiceOverPlaywright.keyboardCommands.openItemChooser,
-            { capture: false },
-          );
-          await delay(500);
-
-          // Filter by "web content" - currently web content items for all browsers
-          // are suffixed by "web content".
-          for (const character of "web content") {
-            await voiceOverPlaywright.type(character, { capture: false });
-            await delay(100);
-          }
-
-          // Select the web content window spot.
-          await voiceOverPlaywright.perform(
-            { keyCode: MacOSKeyCodes.Enter },
-            { capture: false },
-          );
-          await delay(100);
+          // Open item chooser and select web content.
+          await openItemChooser({ voiceOverPlaywright });
+          await selectWebContentItem({ voiceOverPlaywright });
 
           // Navigate into web content.
           await voiceOverPlaywright.interact({ capture: false });
           await delay(100);
 
+          await voiceOverPlaywright.clearSpokenPhraseLog();
+          await voiceOverPlaywright.clearItemTextLog();
+
+          const spokenPhraseLog = await voiceOverPlaywright.spokenPhraseLog();
+          const itemTextLog = await voiceOverPlaywright.itemTextLog();
+
+          spokenPhraseLog.push(...currentSpokenPhraseLog);
+          itemTextLog.push(...currentItemTextLog);
+
           // Navigate to the first element of the page using the provided
           // capture settings.
           await voiceOverPlaywright.next({ capture });