Known Issues in Outlook Email Configuration and How to Resolve Them

The most common Outlook configuration issues with cPanel-hosted email are SSL certificate warnings that appear repeatedly, Outlook asking for your password in an endless loop, "Send test message" failures during setup, email sync delays between devices, and the "Outlook cannot connect to the server" error. Each of these issues has a specific root cause related to how Outlook interprets cPanel mail server settings. This guide documents every known issue with detailed fixes that work on Pakish.net hosting.

Understanding these issues before you encounter them saves hours of frustration and prevents unnecessary email downtime for your business.

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Issue 1: SSL Certificate Warning Keeps Appearing

Symptom

Every time Outlook starts or checks for email, a dialog box appears saying:

"The server you are connected to is using a security certificate that cannot be verified. The target principal name is incorrect."

You click Yes or Continue, but it appears again at the next sync.

Root Cause

On shared hosting, the mail server's SSL certificate is issued for the server's hostname (e.g., server.pakish.net), not for your individual domain name (e.g., mail.yourdomain.com). When Outlook connects to mail.yourdomain.com on port 993, it receives a certificate for a different hostname, triggering the mismatch warning.

Fix Options

Fix 1: Use the Server Hostname Instead (Recommended)

Change your incoming and outgoing server settings to use the hosting server's actual hostname:

1. Open Outlook → File → Account Settings → Account Settings
2. Double-click your email account
3. Change the Incoming mail server from mail.yourdomain.com to the server hostname from your Pakish welcome email (e.g., server.pakish.net or sv1.pakish.net)
4. Change the Outgoing mail server to the same hostname
5. Click Next → Finish

The certificate warning will stop because the certificate matches the hostname.

Fix 2: Install AutoSSL for Mail Subdomain

1. Log into cPanel → SSL/TLS Status
2. Check if mail.yourdomain.com has a valid SSL certificate
3. If not, click Run AutoSSL
4. Wait 5–10 minutes for the certificate to be issued
5. Once issued, mail.yourdomain.com will have a valid certificate and the warning will stop

Fix 3: Accept and Suppress the Warning

If neither option above works:

1. When the certificate dialog appears, check "Always trust this certificate" or "Don't ask me about this server again"
2. Click Yes to accept

This is safe on Pakish servers — the connection is still encrypted, the certificate is just issued for a different hostname.

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Issue 2: Outlook Keeps Asking for Password (Credential Loop)

Symptom

Outlook shows a password dialog box every few minutes. You enter the correct password, but it asks again within seconds or at the next sync cycle. Email does not sync.

Root Cause

This issue has multiple possible causes:

1. SPA is enabled — Outlook is trying Secure Password Authentication, which cPanel does not support
2. Saved credentials are corrupted in Windows Credential Manager
3. Two-factor authentication is enabled on the email account
4. Account password was recently changed but Outlook still uses the old cached credentials

Fix 1: Disable SPA (Most Common Fix)

1. Open Outlook → File → Account Settings → Account Settings
2. Double-click your email account
3. Click More Settings → Outgoing Server tab
4. Uncheck "My outgoing server (SMTP) requires authentication" then re-check it
5. Ensure "Use same settings as my incoming mail server" is selected
6. Go to the Advanced tab
7. Uncheck "This server requires an encrypted connection (SSL)" then re-check it with the correct port
8. Ensure "Require logon using Secure Password Authentication (SPA)" is unchecked for both incoming and outgoing
9. Click OK → Next → Finish

Fix 2: Clear Windows Credential Manager

1. Press Windows Key + R, type control /name Microsoft.CredentialManager, press Enter
2. Click Windows Credentials
3. Look for entries containing your email domain, Outlook, or Office
4. Click each one and click Remove
5. Close Credential Manager
6. Open Outlook — it will ask for your password one more time
7. Enter the correct password and check "Remember my credentials"

Fix 3: Create a New Outlook Profile

If the above fixes do not work, the entire Outlook profile may be corrupted:

1. Close Outlook completely
2. Press Windows Key + R, type control /name Microsoft.Mail, press Enter
3. Click Show Profiles → Add
4. Name the new profile (e.g., "Work Email")
5. Set up your email account from scratch using the correct IMAP settings
6. Set the new profile as default
7. Delete the old corrupted profile

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Issue 3: "Send Test E-mail Message" Fails During Setup

Symptom

When Outlook tests your account settings during setup, the incoming mail test succeeds (green checkmark) but the outgoing mail test fails with:

"Send test e-mail message: Outlook cannot connect to your outgoing (SMTP) mail server."

Root Cause

The SMTP (outgoing) server settings are incorrect, or the ISP is blocking the SMTP port.

Fix 1: Verify SMTP Settings

Ensure these exact values:

| Setting | Correct Value | |---|---| | Outgoing server | mail.yourdomain.com | | Port | 465 | | Encryption | SSL/TLS | | Authentication | Same as incoming (checked) | | SPA | Unchecked |

Fix 2: Try Port 587 (ISP Blocking Fix)

Some Pakistani ISPs (PTCL, Zong 4G) block port 465. Switch to:

| Setting | Value | |---|---| | Port | 587 | | Encryption | STARTTLS |

Fix 3: Check Outgoing Server Authentication

1. Go to More Settings → Outgoing Server tab
2. Check "My outgoing server (SMTP) requires authentication"
3. Select "Use same settings as my incoming mail server"
4. Click OK

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Issue 4: Emails Not Syncing Between Devices

Symptom

You read an email on your phone, but it still shows as unread in Outlook on your laptop. Sent emails from Outlook do not appear in Webmail's Sent folder. Folders created in one place do not appear in the other.

Root Cause

This almost always means you are using POP3 instead of IMAP, or your IMAP folder subscriptions are incorrect.

Fix 1: Confirm You Are Using IMAP

1. In Outlook, go to File → Account Settings → Account Settings
2. Look at the Type column next to your account
3. If it says POP/SMTP instead of IMAP/SMTP, you need to delete and recreate the account using IMAP

Fix 2: Configure IMAP Folder Mapping

1. Go to File → Account Settings → double-click your account
2. Click More Settings → Advanced tab
3. Under Folders, set:
   • Sent Items: Sent
   • Drafts: Drafts
   • Junk/Spam: Junk or spam
   • Trash: Trash
4. Under Root folder path, enter: INBOX
5. Click OK

Fix 3: Subscribe to All Folders

1. Right-click your account name in Outlook's folder pane
2. Select Subscribe to Folders (or IMAP Folders)
3. Click Query to list all available folders
4. Check all folders you want to sync
5. Click Subscribe → OK

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Issue 5: "Outlook Cannot Connect to the Server" Error

Symptom

Outlook shows an error in the bottom status bar: "Disconnected" or "Trying to connect...". No emails are sent or received.

Root Cause

Network connectivity issues, incorrect server settings, or firewall blocking.

Fix 1: Check Internet Connection

Open your browser and try visiting any website. If the internet is down, Outlook cannot connect either. This seems obvious but is the cause in about 30% of reported cases.

Fix 2: Check if Outlook is in "Work Offline" Mode

1. Go to Send/Receive tab in Outlook
2. Check if "Work Offline" is highlighted/active (it should NOT be)
3. If it is active, click it to toggle it off
4. Outlook should immediately attempt to connect

Fix 3: Test Connection with Telnet

Open Command Prompt and test if the mail server port is reachable:

Copytelnet mail.yourdomain.com 993

If you get a connection, the server is reachable. If it times out, the port is blocked by your network or ISP.

Fix 4: Disable Antivirus Email Scanning

Some antivirus programs (especially Kaspersky, Norton, and Avast) intercept email connections for scanning, which can break the SSL connection. Temporarily disable the antivirus email scanning feature and see if Outlook connects.

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Issue 6: Outlook Shows "Not Implemented" Error

Symptom

When sending email, Outlook shows:

"The server responded: 502 5.5.1 Unrecognized command"

or

"Not Implemented"

Root Cause

The encryption method does not match the port. Port 465 requires SSL/TLS, and port 587 requires STARTTLS. Using the wrong combination causes this error.

Fix

Ensure these exact combinations:

| Port | Required Encryption | |---|---| | 465 | SSL/TLS | | 587 | STARTTLS |

Never use port 465 with STARTTLS, or port 587 with SSL/TLS.

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Issue 7: Sent Emails Not Saved to Sent Folder

Symptom

You send an email successfully, but it does not appear in your Sent Items folder in Outlook or Webmail.

Root Cause

IMAP folder mapping is incorrect — Outlook is saving sent items to a local-only folder instead of the server's Sent folder.

Fix

1. Go to File → Account Settings → double-click your account
2. Click More Settings → Advanced tab
3. Under Folders, check "Save sent items in the following folder on the server"
4. Select the Sent folder from the dropdown
5. Click OK

Now test by sending an email. Check both Outlook Sent Items and Webmail Sent folder — both should show the email.

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Issue 8: Outlook Crashes When Opening Specific Emails

Symptom

Outlook freezes or crashes when you click on a specific email, especially HTML-heavy newsletters or emails with large inline images.

Fix

1. Open Outlook in Safe Mode: Press Windows Key + R, type outlook.exe /safe, press Enter
2. In Safe Mode, open the problematic email — if it opens without crashing, an add-in is the cause
3. Go to File → Options → Add-ins → Manage COM Add-ins → Go
4. Uncheck all add-ins, then re-enable them one at a time to find the culprit
5. Common offenders: Grammarly, Adobe Acrobat, or Salesforce add-ins

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Issue 9: Calendar and Contacts Not Syncing

Symptom

IMAP email syncs fine, but calendar events and contacts created in Webmail do not appear in Outlook, and vice versa.

Root Cause

IMAP only syncs email. Calendar and contacts require CalDAV and CardDAV protocols, which Outlook does not natively support for non-Exchange servers.

Workaround Options

1. Use Outlook.com or Microsoft 365 Exchange for calendar and contacts (sync handled by Microsoft's servers)
2. Install CalDAV Synchronizer — a free, open-source Outlook add-in that syncs calendars and contacts with cPanel's CalDAV/CardDAV server
3. Use Google Calendar as an intermediary — sync cPanel calendar to Google Calendar, then Google Calendar to Outlook

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Quick Reference: Port and Encryption Cheat Sheet

| Service | Protocol | Port | Encryption | SPA | |---|---|---|---|---| | Incoming | IMAP | 993 | SSL/TLS | Off | | Incoming | POP3 | 995 | SSL/TLS | Off | | Outgoing | SMTP | 465 | SSL/TLS | Off | | Outgoing | SMTP (alt) | 587 | STARTTLS | Off |

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Frequently Asked Questions

Why does Outlook show a different email count than Webmail?

Outlook only shows emails from subscribed IMAP folders. If you have server-side folders that are not subscribed in Outlook, their emails will not appear. Right-click your account in the folder pane, select IMAP Folders or Subscribe to Folders, query all server folders, and subscribe to any missing ones. After subscribing, click Send Receive All Folders to sync.

Can I use my Pakish email with both Outlook and Gmail?

Yes. Configure your email in Outlook using IMAP (as described in this guide) and add the same account to Gmail using Settings then Accounts and Import then Check mail from other accounts. Both applications will sync with the same server. Because IMAP keeps everything on the server, both clients always show the same emails.

Outlook says my password is wrong, but I can log into Webmail with the same password. Why?

This is almost always caused by SPA (Secure Password Authentication) being enabled in Outlook. SPA uses a different authentication protocol that cPanel does not support. Go to your account settings, click More Settings, and ensure SPA is unchecked on both incoming and outgoing tabs. Also check Windows Credential Manager for old saved credentials that might be overriding what you type.

How do I export all my Outlook emails before reconfiguring?

Go to File then Open and Export then Import Export then Export to a file then Outlook Data File (.pst). Select the folders you want to export (or your entire account) and choose a save location. The .pst file contains all emails, folders, contacts, and calendar entries. After reconfiguring your account, you can import this file back using the same wizard.

My company switched from POP3 to IMAP. Will I lose my old emails?

No. Your old emails downloaded via POP3 are stored locally in your Outlook data file (.pst). When you set up the new IMAP account, you will see two email accounts in your Outlook folder pane — the old POP3 and the new IMAP. You can drag and drop emails from the POP3 folders to the IMAP folders, and they will be uploaded to the server, making them accessible from all devices.