Email Troubleshooting Guide

1. Introduction

This guide is designed to help you diagnose and resolve email-related issues within your Ezy Systems software. Email functionality in our software relies on your existing email infrastructure — Ezy Systems has not made any recent changes to the core email code, meaning issues are typically caused by changes in your email environment, server configuration, or security settings.

This document will walk you through a series of diagnostic questions and step-by-step troubleshooting actions. If you are unable to resolve the issue yourself, the technical section at the end of this guide provides information you can share directly with your IT provider.

2. Understanding the "Success" Message

This is one of the most important things to understand before troubleshooting email in your Ezy Systems software. Please read this section carefully.

⚠ IMPORTANT: What "Success" Actually Means

**The "Success" or "Email Sent" message in Ezy Systems software does NOT mean your email has been delivered to the recipient.

It means only this: the email was successfully handed off to your SMTP server or third-party email application (such as Outlook or your mail relay service).

What happens AFTER that handoff is entirely outside of Ezy Systems' control and depends on your email infrastructure, your internet service provider, and the recipient's mail server.

Think of it like dropping a letter in a post box — our software confirms the letter went into the box. Whether Australia Post delivers it is a separate matter entirely.

Why Does This Matter?

Many reported email issues fall into this category: the software shows "Success" but the recipient never receives the email. This is almost always caused by one of the following happening after the handoff:

The SMTP server accepted the email but then rejected or bounced it due to authentication or policy issues.
The email was quarantined by a spam filter (at your end or the recipient's end) after leaving your SMTP server.
The SMTP server placed the email in a queue due to a temporary issue, causing a delay — sometimes minutes, sometimes hours.
The recipient's mail server rejected the email (e.g., due to your domain's SPF/DKIM/DMARC configuration).
A relay or forwarding rule intercepted the email before it reached the recipient.

In all of these cases, the software correctly reported "Success" because it did its job — it delivered the email to the handoff point. The investigation must focus on what happened after that point, which is why the IT provider steps in Section 4 are so important.

3. Initial Diagnostic Questions

Before beginning troubleshooting, please work through the following questions. Your answers will help narrow down the cause of the issue quickly.

3.1 When Did This Start?

Understanding the timeline is critical. Please note:

What is the exact date the issue first occurred?
Did anything change around that time? (e.g., Windows or Office updates, password changes, new IT policy, server migration, new antivirus/firewall)
Was the issue sudden (worked one day, not the next) or gradual?
Has this issue occurred before? If so, how was it resolved?

3.2 Who Is Affected?

Is this affecting one specific user, multiple users, or all users?
Is this a brand-new user who has never had email working in the software, or an existing user who previously had it working?
If multiple users — are they on the same machine, same office/location, or spread across different sites?
Are users on the same domain/Active Directory group?

3.3 What Email Platform Are You Using?

Microsoft 365 (formerly Office 365)
Microsoft Exchange (on-premises)
Gmail / Google Workspace
Other SMTP provider (e.g., SendGrid, Mailgun, hosting provider SMTP)
Are you using OAuth 2.0 / Modern Authentication, or Basic Authentication (username & password)?

3.4 What Exactly Is Happening?

Are emails failing to send, failing to receive, or both?
Is there an error message displayed? If so, please note the exact wording.
Are emails sent from within the software but never arriving at the destination?
Are emails going to the Junk/Spam folder of the recipient?
Is the email appearing to send successfully in the software, but the recipient never receives it?
Does the issue affect all email types (invoices, statements, job notifications) or only specific ones?

3.5 Recent Changes to Your Environment

The most common cause of email issues is a change in the email environment rather than the software itself. Please check:

Has your Microsoft 365 or Exchange admin recently updated security policies?
Has your email password been changed recently?
Has Multi-Factor Authentication (MFA) been enabled on the sending email account?
Has your organisation migrated from on-premises Exchange to Microsoft 365?
Has a new firewall, proxy, or security appliance been installed?
Has your IT provider changed your SMTP relay settings?
Has your email domain been moved to a different hosting provider?

4. Step-by-Step Troubleshooting Guide

Follow each step in order. Many issues are resolved at Step 1 or 2. If you complete all steps without resolution, proceed to Section 4 for IT provider escalation.

STEP 1

Verify Your Email Settings in the Software

Open your Ezy Systems software and navigate to the Email Configuration / Settings area.
Confirm the SMTP server address is correct for your email provider (see reference table in Section 5).
Confirm the port number is correct (common ports: 587 for TLS/STARTTLS, 465 for SSL, 25 for relay).
Confirm the "From" email address matches the account being authenticated.
Confirm the username/email address used for authentication is correct.
Re-enter your email password — even if you believe it is correct, passwords can expire or be changed by IT policy without your knowledge.
Ensure SSL/TLS encryption setting matches what your email provider requires.
Save settings and perform a test send.

STEP 2

Check for Recent Password or MFA Changes

Log in to your email account (e.g., Outlook Web App, Gmail) using the same credentials entered in the software.
If you cannot log in with your normal password — your password has changed. Update it in the software settings.
If Microsoft 365 has MFA (Multi-Factor Authentication) enabled on this account, Basic Authentication (username + password) will no longer work. You will need to use OAuth 2.0 / App Passwords instead (see Step 4).
If using Microsoft 365, check whether your admin has disabled Basic Authentication. This is a very common cause of email issues as Microsoft rolled out these changes globally.

STEP 3

Test Email Directly from Your Email Client

Open Outlook (or your standard email client) on the same computer.
Send a test email to yourself or a colleague.
If this also fails, the issue is with your email account or server — not the Ezy Systems software. Contact your IT provider.
If Outlook works but the software does not, the issue is in the software's email configuration — continue to Step 4.

STEP 4

Microsoft 365 — OAuth and App Password Settings

Modern Authentication (OAuth 2.0) — If your organisation uses Microsoft 365 with Modern Authentication, the software must be configured to use OAuth. Please contact Ezy Systems support for guidance on setting this up.
App Passwords (if MFA is enabled) — If MFA is enabled on the sending account, you must generate an App Password in your Microsoft 365 account settings and use that in place of your regular password in the software.
To generate an App Password: log in to account.microsoft.com → Security → Advanced Security Options → App Passwords → Create.
SMTP AUTH must be enabled on the mailbox in Microsoft 365 Admin Centre. Ask your IT provider to confirm: Exchange Admin Centre → Mailboxes → select user → Mail Flow Settings → SMTP AUTH = Enabled.

STEP 5

Check Firewall and Antivirus Settings

Some firewall and antivirus products block outbound SMTP connections from applications they do not recognise.
Temporarily disable your antivirus or firewall (on a test basis only) and attempt to send a test email from the software.
If email works with the firewall/AV disabled, an exception rule needs to be added for the Ezy Systems application. Contact your IT provider.
Ensure outbound traffic is permitted on port 587 (or whichever port your email provider uses).

STEP 6

For New Users — Check Account Setup

Confirm that the new user's email account has been fully provisioned in your email system (Microsoft 365, Exchange, etc.).
Ensure the user has been assigned an appropriate email licence (Microsoft 365 requires a licence for each mailbox).
If the new user is using a shared mailbox or a generic "no-reply" address, ensure SMTP AUTH is enabled on that specific mailbox.
Confirm the user has the correct permissions within the Ezy Systems software to send emails.
If the new user is on a different machine to other staff, ensure the email ports (587/465/25) are not blocked by local firewall or group policy on that machine.

STEP 7

Check Spam / Junk Filtering

If emails are being sent but not received, ask the recipient to check their Junk or Spam folder.
Check whether your email domain has SPF, DKIM, and DMARC records configured correctly — missing or incorrect DNS records cause emails to be treated as spam.
Ask your IT provider to review the mail flow logs in Microsoft 365 or Exchange to confirm whether emails are leaving your server.
If using a third-party spam filter (e.g., Mimecast, Proofpoint), check whether emails are being quarantined there.

STEP 8

Review Error Messages

Note the exact error message shown in the software.
Common errors and their meanings are listed in Section 6 of this document.
Take a screenshot of the error and include it when contacting support.
If no error is shown but emails are not arriving, check the sent items of the email account used for sending.
This step applies to customers using the legacy Ezy Systems FoxPro-based product only.
Navigate to your Ezy Systems root installation folder on the server (e.g., C:\EZY or the network path your system uses).
Inside the Ezy root folder, locate the TMP folder.
In the TMP folder, look for the email report file — this file records all communications between the software and your SMTP server.
Open the report file in Notepad or a text editor and review the contents.
This report will show you the exact responses received from your SMTP server for each send attempt.
IMPORTANT: This information may appear with a delay. The software may display "Success" before the SMTP server's response has been fully written to this file. If the file appears empty or incomplete, wait a few minutes and check again.
If the report shows an error code or rejection message from the SMTP server, note the exact wording and include it when contacting Ezy Systems support — this is the most accurate diagnosis of what went wrong after the handoff.
If the report shows "250 OK" or similar acceptance codes but the email was still not received, the issue occurred further downstream (spam filter, relay, or recipient server).

STEP 9

Legacy Product (FoxPro) Users — Check the TMP Folder Email Report

This step applies to customers using the legacy Ezy Systems FoxPro-based product only.
Navigate to your Ezy Systems root installation folder on the server (e.g., C:\EZY or the network path your system uses).
Inside the Ezy root folder, locate the TMP folder.
In the TMP folder, look for the email report file — this file records all communications between the software and your SMTP server.
Open the report file in Notepad or a text editor and review the contents.
This report will show you the exact responses received from your SMTP server for each send attempt.
IMPORTANT: This information may appear with a delay. The software may display "Success" before the SMTP server's response has been fully written to this file. If the file appears empty or incomplete, wait a few minutes and check again.
If the report shows an error code or rejection message from the SMTP server, note the exact wording and include it when contacting Ezy Systems support — this is the most accurate diagnosis of what went wrong after the handoff.
If the report shows "250 OK" or similar acceptance codes but the email was still not received, the issue occurred further downstream (spam filter, relay, or recipient server).

5. Technical Information for Your IT Provider

If you have been unable to resolve the issue using the steps above, please share this section with your IT provider. It contains the technical detail they will need to investigate further.

5.1 How Ezy Systems Software Sends Email

Ezy Systems software uses SMTP (Simple Mail Transfer Protocol) to send emails. The software does not maintain its own mail server — it connects to your organisation's email infrastructure using the credentials and server settings configured in the application. No recent changes have been made to the email-sending code within the software.

5.2 Required SMTP Configuration

Setting	Detail
Protocol	SMTP
Encryption	TLS / STARTTLS (preferred) or SSL
Authentication	Username + Password (Basic Auth) or OAuth 2.0
Typical Ports	587 (STARTTLS), 465 (SSL), 25 (relay — not recommended)
From Address	Must match the authenticated mailbox
SMTP AUTH	Must be enabled on the sending mailbox (critical for M365)

5.3 Microsoft 365 — Key Checks for IT Providers

Confirm SMTP AUTH is enabled for the sending mailbox: Exchange Admin Centre → Mailboxes → [user] → Mail Flow Settings → Authenticated SMTP = ON.
Confirm Basic Authentication has not been disabled at the tenant level via Authentication Policies or Conditional Access policies.
Review the Message Trace in Microsoft 365 Admin Centre (Security & Compliance → Mail Flow → Message Trace) to confirm whether messages are leaving the tenant.
If Modern Authentication is required, the application will need to authenticate via OAuth 2.0 — please contact Ezy Systems support to discuss configuration options.
Verify the sending account has an active Exchange Online licence with a mailbox provisioned.
Check whether a Conditional Access policy is blocking the SMTP connection from the client machine's IP address or device.

5.4 On-Premises Exchange — Key Checks for IT Providers

Confirm the SMTP relay connector is configured to accept connections from the client machines/IP range running Ezy Systems software.
Check the Exchange transport logs for any rejected or failed relay attempts.
Ensure TLS certificates on the Exchange server are valid and not expired.
If using an internal SMTP relay, confirm the relay server is whitelisted and not blocking the application.

5.5 DNS Record Verification (Anti-Spam)

Poor DNS configuration causes legitimate emails to be flagged as spam. Please verify all three records are in place:

Record Type	Purpose
SPF (TXT)	Lists which mail servers are authorised to send on behalf of your domain. Must include your SMTP relay/M365 server.
DKIM	Digitally signs outbound emails to prove they were not tampered with in transit. Must be enabled in M365 or Exchange.
DMARC (TXT)	Tells receiving servers what to do if SPF/DKIM fail. Prevents spoofing and improves deliverability.

5.6 Firewall and Network Requirements

Outbound TCP port 587 (STARTTLS) or 465 (SSL) must be open from all machines running Ezy Systems software to the SMTP server.
The Ezy Systems application executable must be whitelisted/permitted in any application-layer firewall or endpoint security product (e.g., Sophos, CrowdStrike, Defender for Endpoint).
If using a proxy server for outbound internet traffic, confirm the SMTP traffic is not being intercepted or blocked by the proxy.
Some ISPs block port 25 — ensure port 587 or 465 is being used as the outbound SMTP port.

5.7 Diagnostic Commands for IT Providers

Test SMTP Connectivity (Run from affected machine — Command Prompt or PowerShell)

Test port 587 connectivity:

Test-NetConnection -ComputerName smtp.office365.com -Port 587

Test port 465 connectivity:

Test-NetConnection -ComputerName smtp.office365.com -Port 465

Telnet test (if telnet client is enabled):

telnet smtp.office365.com 587

Check if SMTP AUTH is enabled for a mailbox (Exchange Online PowerShell):

Get-CASMailbox -Identity user@domain.com | Select SmtpClientAuthenticationDisabled

Enable SMTP AUTH for a specific mailbox:

Set-CASMailbox -Identity user@domain.com -SmtpClientAuthenticationDisabled $false

6. Common SMTP Server Settings Reference

Email Provider	SMTP Settings
Microsoft 365	Server: smtp.office365.com \| Port: 587 \| Encryption: STARTTLS \| Auth: Required
Gmail / Google Workspace	Server: smtp.gmail.com \| Port: 587 \| Encryption: TLS \| Auth: Required (App Password if 2FA enabled)
On-Premises Exchange	Server: your internal Exchange server address \| Port: 587 or 25 \| Encryption: TLS or None \| Auth: Required or anonymous relay
Outlook.com (personal)	Server: smtp-mail.outlook.com \| Port: 587 \| Encryption: STARTTLS \| Auth: Required

7. Common Error Messages and Meanings

Error Message	Likely Cause & Action
535 Authentication failed	Incorrect username or password. Verify credentials. If M365 with MFA enabled, use an App Password.
530 5.7.0 Authentication required	SMTP AUTH is disabled on this mailbox in M365. IT provider needs to enable it via Exchange Admin Centre.
550 5.7.60 SMTP client does not have permissions	The sending account does not have Send As or SMTP AUTH permission. Contact your IT provider.
Connection timed out / Unable to connect	Firewall is blocking the SMTP port. Check ports 587/465 are open outbound from this machine.
553 Relaying not allowed	The SMTP server is not configured to relay email for your domain or IP. Update relay connector or use authenticated SMTP.
550 Message rejected as spam	SPF/DKIM/DMARC records may be misconfigured, or sending IP is blacklisted. Contact IT provider to check DNS records.
TLS negotiation failed	TLS certificate on the mail server is expired or the encryption settings do not match. Contact IT provider.
421 Service temporarily unavailable	The mail server is temporarily overloaded or unreachable. Wait a few minutes and retry. If persistent, contact IT.

8. Related Documents

The following companion documents are available from Ezy Systems and should be read alongside this guide:

Document	Purpose
Office 365 SMTP Relay Setup Guide	Step-by-step configuration guide for setting up a Microsoft 365 SMTP relay connector using your Ezy Server's static IP address. Use this when configuring email for the first time with M365, or when switching to the relay method. Includes screenshots of the Exchange Admin Centre setup process.
Email Troubleshooting Guide (this document)	Diagnostic questions, step-by-step troubleshooting, and IT provider technical reference for resolving email issues once setup is complete.

When to use the Office 365 SMTP Relay Setup Guide:

You are configuring M365 email in Ezy Systems for the first time.
Your IT provider has set up (or recommends) a relay connector approach using a static IP address rather than standard SMTP authentication.
You are an Ezy Cloud customer and have been provided a static IP address by Ezy Systems support.
You need to re-configure the connector after a server migration or IP address change.

9. When to Contact Ezy Systems Support

Please contact the Ezy Systems support team if:

You have completed all steps in this guide and the issue remains unresolved.
You need assistance configuring OAuth 2.0 / Modern Authentication for Microsoft 365.
You are receiving an error message not listed in Section 6.
Email was previously working and stopped after a software update (though no recent email-related changes have been made to our software, we are happy to investigate).
You are setting up email for the first time and need guidance on initial configuration.

Ezy Systems Support — What to Include in Your Support Request

1. The exact error message displayed (screenshot preferred)

2. The email provider you are using (M365, Exchange, Gmail, etc.)

3. When the issue started and what changed around that time

4. How many users are affected

5. Whether the issue is specific to a new user or affects existing users

6. What troubleshooting steps you have already attempted

7. Results of any IT provider checks (e.g., SMTP AUTH status, message trace)

10. Quick Reference Checklist

Use this checklist when reporting an email issue to ensure all basic checks have been completed:

Check	Status
SMTP server address verified in software settings	☐ Complete ☐ N/A
Port number confirmed correct	☐ Complete ☐ N/A
Email password re-entered/confirmed	☐ Complete ☐ N/A
Can log in to email account via web browser with same credentials	☐ Complete ☐ N/A
Outlook / email client sends successfully from same machine	☐ Complete ☐ N/A
MFA/2FA status confirmed on sending account	☐ Complete ☐ N/A
App Password generated (if MFA enabled on M365)	☐ Complete ☐ N/A
SMTP AUTH enabled on mailbox (M365/Exchange)	☐ Complete ☐ N/A
Firewall/antivirus temporarily disabled for testing	☐ Complete ☐ N/A
Outbound port 587 confirmed open from affected machine	☐ Complete ☐ N/A
Recipient junk/spam folder checked	☐ Complete ☐ N/A
SPF, DKIM, DMARC records verified with IT provider	☐ Complete ☐ N/A
Error message screenshot captured	☐ Complete ☐ N/A
(FoxPro only) TMP folder email report reviewed	☐ Complete ☐ N/A
Understood: "Success" = handed to SMTP only, not final delivery	☐ Confirmed