diff --git a/packages/app-tests/e2e/document-flow/autosave-subject-step.spec.ts b/packages/app-tests/e2e/document-flow/autosave-subject-step.spec.ts
index 64e9a41bf..404a03ae1 100644
--- a/packages/app-tests/e2e/document-flow/autosave-subject-step.spec.ts
+++ b/packages/app-tests/e2e/document-flow/autosave-subject-step.spec.ts
@@ -106,10 +106,10 @@ test.describe('AutoSave Subject Step', () => {
     const { user, document, team } = await setupDocumentAndNavigateToSubjectStep(page);
 
     // Toggle some email settings checkboxes (randomly - some checked, some unchecked)
-    await page.getByText('Send recipient signed email').click();
-    await page.getByText('Send recipient removed email').click();
-    await page.getByText('Send document completed email', { exact: true }).click();
-    await page.getByText('Send document deleted email').click();
+    await page.getByText('Email the owner when a recipient signs').click();
+    await page.getByText("Email recipients when they're removed from a pending document").click();
+    await page.getByText('Email recipients when the document is completed', { exact: true }).click();
+    await page.getByText('Email recipients when a pending document is deleted').click();
 
     await triggerAutosave(page);
 
@@ -126,26 +126,30 @@ test.describe('AutoSave Subject Step', () => {
 
       const emailSettings = retrievedDocumentData.documentMeta?.emailSettings;
 
-      await expect(page.getByText('Send recipient signed email')).toBeChecked({
+      await expect(page.getByText('Email the owner when a recipient signs')).toBeChecked({
         checked: emailSettings?.recipientSigned,
       });
-      await expect(page.getByText('Send recipient removed email')).toBeChecked({
+      await expect(
+        page.getByText("Email recipients when they're removed from a pending document"),
+      ).toBeChecked({
         checked: emailSettings?.recipientRemoved,
       });
-      await expect(page.getByText('Send document completed email', { exact: true })).toBeChecked({
+      await expect(
+        page.getByText('Email recipients when the document is completed', { exact: true }),
+      ).toBeChecked({
         checked: emailSettings?.documentCompleted,
       });
-      await expect(page.getByText('Send document deleted email')).toBeChecked({
+      await expect(page.getByText('Email recipients when a pending document is deleted')).toBeChecked({
         checked: emailSettings?.documentDeleted,
       });
 
-      await expect(page.getByText('Send recipient signing request email')).toBeChecked({
+      await expect(page.getByText('Email recipients with a signing request')).toBeChecked({
         checked: emailSettings?.recipientSigningRequest,
       });
-      await expect(page.getByText('Send document pending email')).toBeChecked({
+      await expect(page.getByText('Email the signer if the document is still pending')).toBeChecked({
         checked: emailSettings?.documentPending,
       });
-      await expect(page.getByText('Send document completed email to the owner')).toBeChecked({
+      await expect(page.getByText('Email the owner when the document is completed')).toBeChecked({
         checked: emailSettings?.ownerDocumentCompleted,
       });
     }).toPass();
@@ -161,10 +165,10 @@ test.describe('AutoSave Subject Step', () => {
     await page.getByRole('textbox', { name: 'Subject (Optional)' }).fill(subject);
     await page.getByRole('textbox', { name: 'Message (Optional)' }).fill(message);
 
-    await page.getByText('Send recipient signed email').click();
-    await page.getByText('Send recipient removed email').click();
-    await page.getByText('Send document completed email', { exact: true }).click();
-    await page.getByText('Send document deleted email').click();
+    await page.getByText('Email the owner when a recipient signs').click();
+    await page.getByText("Email recipients when they're removed from a pending document").click();
+    await page.getByText('Email recipients when the document is completed', { exact: true }).click();
+    await page.getByText('Email recipients when a pending document is deleted').click();
 
     await triggerAutosave(page);
 
@@ -190,26 +194,30 @@ test.describe('AutoSave Subject Step', () => {
         retrievedDocumentData.documentMeta?.message ?? '',
       );
 
-      await expect(page.getByText('Send recipient signed email')).toBeChecked({
+      await expect(page.getByText('Email the owner when a recipient signs')).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.recipientSigned,
       });
-      await expect(page.getByText('Send recipient removed email')).toBeChecked({
+      await expect(
+        page.getByText("Email recipients when they're removed from a pending document"),
+      ).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.recipientRemoved,
       });
-      await expect(page.getByText('Send document completed email', { exact: true })).toBeChecked({
+      await expect(
+        page.getByText('Email recipients when the document is completed', { exact: true }),
+      ).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.documentCompleted,
       });
-      await expect(page.getByText('Send document deleted email')).toBeChecked({
+      await expect(page.getByText('Email recipients when a pending document is deleted')).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.documentDeleted,
       });
 
-      await expect(page.getByText('Send recipient signing request email')).toBeChecked({
+      await expect(page.getByText('Email recipients with a signing request')).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.recipientSigningRequest,
       });
-      await expect(page.getByText('Send document pending email')).toBeChecked({
+      await expect(page.getByText('Email the signer if the document is still pending')).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.documentPending,
       });
-      await expect(page.getByText('Send document completed email to the owner')).toBeChecked({
+      await expect(page.getByText('Email the owner when the document is completed')).toBeChecked({
         checked: retrievedDocumentData.documentMeta?.emailSettings?.ownerDocumentCompleted,
       });
     }).toPass();
diff --git a/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts b/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
index 795fec9ff..400f635ba 100644
--- a/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
+++ b/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
@@ -205,9 +205,13 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
   await page.getByRole('textbox', { name: 'Reply to email' }).fill('organisation@documenso.com');
 
   // Update email document settings by enabling/disabling some checkboxes
-  await page.getByRole('checkbox', { name: 'Send recipient signed email' }).uncheck();
-  await page.getByRole('checkbox', { name: 'Send document pending email' }).uncheck();
-  await page.getByRole('checkbox', { name: 'Send document deleted email' }).uncheck();
+  await page.getByRole('checkbox', { name: 'Email the owner when a recipient signs' }).uncheck();
+  await page
+    .getByRole('checkbox', { name: 'Email the signer if the document is still pending' })
+    .uncheck();
+  await page
+    .getByRole('checkbox', { name: 'Email recipients when a pending document is deleted' })
+    .uncheck();
 
   await page.getByRole('button', { name: 'Update' }).first().click();
   await expect(page.getByText('Your email preferences have been updated').first()).toBeVisible();
@@ -240,12 +244,14 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
   await page.getByRole('option', { name: 'Override organisation settings' }).click();
 
   // Update some email settings
-  await page.getByRole('checkbox', { name: 'Send recipient signing request email' }).uncheck();
   await page
-    .getByRole('checkbox', { name: 'Send document completed email', exact: true })
+    .getByRole('checkbox', { name: 'Email recipients with a signing request' })
     .uncheck();
   await page
-    .getByRole('checkbox', { name: 'Send document completed email to the owner' })
+    .getByRole('checkbox', { name: 'Email recipients when the document is completed', exact: true })
+    .uncheck();
+  await page
+    .getByRole('checkbox', { name: 'Email the owner when the document is completed' })
     .uncheck();
 
   await page.getByRole('button', { name: 'Update' }).first().click();
diff --git a/packages/ui/components/document/document-email-checkboxes.tsx b/packages/ui/components/document/document-email-checkboxes.tsx
index 884dc5e6c..a1c35c828 100644
--- a/packages/ui/components/document/document-email-checkboxes.tsx
+++ b/packages/ui/components/document/document-email-checkboxes.tsx
@@ -37,7 +37,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.RecipientSigned}
         >
-          <Trans>Send recipient signed email</Trans>
+          <Trans>Email the owner when a recipient signs</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -75,7 +75,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.RecipientSigningRequest}
         >
-          <Trans>Send recipient signing request email</Trans>
+          <Trans>Email recipients with a signing request</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -113,7 +113,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.RecipientRemoved}
         >
-          <Trans>Send recipient removed email</Trans>
+          <Trans>Email recipients when they're removed from a pending document</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -151,7 +151,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.DocumentPending}
         >
-          <Trans>Send document pending email</Trans>
+          <Trans>Email the signer if the document is still pending</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -190,7 +190,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.DocumentCompleted}
         >
-          <Trans>Send document completed email</Trans>
+          <Trans>Email recipients when the document is completed</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -228,7 +228,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.DocumentDeleted}
         >
-          <Trans>Send document deleted email</Trans>
+          <Trans>Email recipients when a pending document is deleted</Trans>
 
           <Tooltip>
             <TooltipTrigger>
@@ -266,7 +266,7 @@ export const DocumentEmailCheckboxes = ({
           className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
           htmlFor={DocumentEmailEvents.OwnerDocumentCompleted}
         >
-          <Trans>Send document completed email to the owner</Trans>
+          <Trans>Email the owner when the document is completed</Trans>
 
           <Tooltip>
             <TooltipTrigger>