diff --git a/config/locales/server.en.yml b/config/locales/server.en.yml
index 7447183e3..84512bf6f 100644
--- a/config/locales/server.en.yml
+++ b/config/locales/server.en.yml
@@ -1779,21 +1779,21 @@ en:
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        The original notification was not sent to this email address. Try sending from a different email address, or contact a staff member.
+        Your reply was sent from a different email address than the one we expected, so we're not sure if this is the same person. Try sending from another email address, or contact a staff member.
 
     email_reject_no_message_id:
       subject_template: "[%{site_name}] Email issue -- No Message Id"
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        There was no Message-Id header in the email. Try sending from a different email address, or contact a staff member.
+        We couldn't find a `Message-Id` header in the email. Try sending from a different email address, or contact a staff member.
 
     email_reject_no_account:
       subject_template: "[%{site_name}] Email issue -- Unknown Account"
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        There is no known user account with this email address. Try sending from a different email address, or contact a staff member.
+        We can't find any accounts that match your email address. Try sending from a different email address, or contact a staff member.
 
     email_reject_empty:
       subject_template: "[%{site_name}] Email issue -- No Content"
@@ -1856,21 +1856,21 @@ en:
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        The provided reply key is invalid or unknown, so we don't know what this email is in reply to. Contact a staff member.
+        The reply key in the email is invalid or unknown, so we can't figure out what this email is in reply to. Contact a staff member.
 
     email_reject_bad_destination_address:
       subject_template: "[%{site_name}] Email issue -- Unknown To: Address"
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        None of the destination addresses are recognized. Please make sure that you are sending to the correct email address provided by staff.
+        None of the destination email addresses are recognized. Please make sure that you are sending to the correct email address provided by staff.
 
     email_reject_topic_not_found:
       subject_template: "[%{site_name}] Email issue -- Topic Not Found"
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        The topic you are replying to no longer exists, perhaps it was deleted? If you believe this is in error, contact a staff member.
+        The topic you are replying to no longer exists -- perhaps it was deleted? If you believe this is in error, contact a staff member.
 
     email_reject_topic_closed:
       subject_template: "[%{site_name}] Email issue -- Topic Closed"
@@ -1884,7 +1884,7 @@ en:
       text_body_template: |
         We're sorry, but your email message to %{destination} (titled %{former_title}) didn't work.
 
-        Your email was marked as "auto generated", which we can't accept. If you believe this is in error, contact a staff member.
+        Your email was marked as "auto generated", which means it was automatically created by a computer instead of being typed by a human; we can't accept those kinds of emails. If you believe this is in error, contact a staff member.
 
     email_error_notification:
       subject_template: "[%{site_name}] Email issue -- POP authentication error"
@@ -1893,6 +1893,8 @@ en:
 
         Please make sure you have properly configured the POP credentials in [the site settings](%{base_url}/admin/site_settings/category/email).
 
+        If there is a web UI, you may need to log in on the web and check your settings.
+
     too_many_spam_flags:
       subject_template: "New account blocked"
       text_body_template: |