Emails Not Sending? Fix Common Email Issues Easily

For Auckland businesses, email is an essential daily tool. From customer communications and invoicing to internal collaboration, reliable email is critical. However, it’s frustrating—and potentially damaging—when emails fail to send, get stuck in your outbox, or bounce back without explanation.

This guide is an extension of our email and Internet Set Up Services and explains how to troubleshoot common email sending issues quickly and easily. Whether you’re using Outlook, Gmail, or another platform, we’ll cover practical steps to resolve the most common email sending problems businesses face. Plus, we’ll highlight when professional IT support from Auckland Geeks can quickly restore normal business operations, preventing downtime and lost productivity.

Common Reasons Emails Fail to Send

Before diving into troubleshooting solutions, it’s useful to understand what usually causes email sending issues in business environments:

• SMTP (Outgoing Mail Server) misconfigurations: Incorrect settings prevent your emails from leaving the outbox.
• Large attachment size limits: Emails with large attachments may be blocked or fail to send.
• ISP or server issues: Temporary outages or server maintenance causing disruption.
• Incorrect security settings: Authentication or encryption issues leading to bounced emails.
• Spam or filtering issues: Your email might unintentionally trigger spam filters.
• Device synchronisation errors: Emails sometimes appear stuck if your device is not correctly syncing with the mail server.

Let’s look at each issue in detail and discuss how you can easily resolve or diagnose these issues yourself.

Practical Steps to Quickly Fix Common Email Sending Problems

1. Check SMTP Server Settings (Outgoing Mail Settings)

Problem:
One of the most frequent email sending problems relates to incorrect SMTP settings. SMTP (Simple Mail Transfer Protocol) is the standard technology for sending emails.

How to Fix:

• Open your email application (e.g., Outlook or Gmail) and review your outgoing SMTP server settings.
• Ensure that the outgoing mail server address matches your email provider’s recommended settings (e.g., smtp.gmail.com for Gmail or your Outlook provider’s SMTP server).
• Verify the port number—typically 587 (secure TLS) or 465 (SSL)—is correctly configured.
• Check if authentication is enabled (required for most business email providers like Microsoft 365 or Google Workspace).
• Double-check usernames and passwords—typos here often cause emails to fail.

Attachment Size and Email Limits

Issue: Emails getting stuck due to large attachments

Many email providers impose size limits on attachments (typically around 25 MB). Larger files often get stuck in the outbox or trigger bounce-backs.

Quick fix tips:

• Check your email provider’s maximum allowed attachment size.
• Compress large files using ZIP or cloud-based sharing platforms like Dropbox, OneDrive, or Google Drive.
• For larger files, consider sharing download links via cloud storage services rather than attachments.

Emails Flagged as Spam or Bounced

Issue: Emails not reaching recipients due to spam filters or blacklisting

Emails can fail to send if your email address or domain has been blacklisted or if your emails trigger spam filters.

Quick solutions:

• Check your domain’s spam reputation using free tools like MXToolbox or Google Postmaster.
• Ensure your domain’s DNS records (SPF, DKIM, DMARC) are correctly configured—these records prove your emails are legitimate.
• Adjust email content to avoid spam-like characteristics, such as excessive capital letters, numerous links, or suspicious wording.

When to Call Auckland Geeks:
Resolving blacklisting or DNS issues can be complex. Auckland Geeks can expertly handle this, quickly restoring your email’s reputation and deliverability.

Device Synchronisation Issues

Issue: Emails appear stuck or aren’t sending due to device sync errors

If your emails aren’t synchronising properly between devices, emails can appear stuck, causing confusion.

Easy troubleshooting steps:

• Refresh your email application or restart your device, as temporary glitches often fix themselves.
• Ensure that your devices are configured to use IMAP rather than POP3—IMAP ensures emails and folders synchronise smoothly across devices.
• Verify your device’s internet connectivity—poor connectivity or intermittent internet connections can stall outgoing emails.

If persistent, professional assistance from Auckland Geeks can swiftly resolve more complicated device synchronisation issues.

Email Security and Authentication Errors

Issue: Emails bouncing due to authentication or security settings

Sometimes your email provider requires additional authentication methods, and failing to provide these can cause emails to bounce.

Quick fix tips:

• Ensure your outgoing server requires authentication is ticked (in Outlook, “My server requires authentication” setting).
• Check encryption settings (typically SSL/TLS) match your provider’s recommendations.
• Enable Two-Factor Authentication (2FA) and generate app-specific passwords if required (particularly relevant for Microsoft 365 and Gmail users).

Auckland Geeks can set up advanced security and authentication correctly, avoiding future disruptions.

Temporary Server Outages

Issue: ISP or email provider temporary outages

Occasionally, email providers face temporary outages. These disruptions typically resolve themselves within a short period.

How to check:

• Visit your email provider’s status page (e.g., Microsoft 365 Service Status or Gmail Status Dashboard).
• Confirm via social media or online outage trackers like Downdetector.co.nz.
• If your provider confirms an outage, simply wait—it usually resolves quickly without intervention.

However, prolonged or frequent outages should be addressed professionally. Auckland Geeks can help identify long-term solutions or reliable alternatives.

When Should You Call Auckland Geeks?

While minor email issues can often be fixed quickly yourself, professional assistance becomes crucial in scenarios like:

• Persistent SMTP or DNS errors: Expert diagnostics and configurations are required to ensure your email system reliably delivers messages.
• Email migration and advanced setup: Transferring emails between providers (e.g., moving from Xtra Mail to Microsoft 365 or Google Workspace) involves complicated processes that require professional oversight to prevent data loss.
• Complex spam filtering or blacklisting issues: Custom spam filters and DNS corrections require technical expertise.
• Advanced security configurations: Implementing professional-grade email security (e.g., advanced spam filtering, encryption, or two-factor authentication) benefits significantly from professional setup.

Auckland Geeks provide swift, reliable email support, ensuring your business communication remains seamless and secure.

Preventative Measures to Avoid Email Issues in Future

Taking proactive steps reduces the risk of future email disruptions:

• Use professional email hosting services: Platforms like Microsoft 365 and Google Workspace offer robust reliability, synchronisation, and security features, significantly reducing future issues.
• Regularly update and audit your email settings: Prevent common email issues by routinely verifying SMTP configurations and security settings.
• Train your staff in basic email troubleshooting: Empowering your team reduces downtime and resolves minor email disruptions quickly.
• Schedule regular IT reviews: Auckland Geeks can perform periodic health checks of your email system, proactively preventing potential issues before they impact your business.

Keep Your Business Emails Flowing with Auckland Geeks

Email problems are frustrating, but they don’t have to disrupt your business operations. With basic troubleshooting knowledge, minor email issues can be resolved swiftly. Yet when issues persist or become complex, professional IT support from Auckland Geeks ensures fast resolution and long-term reliability.

Auckland Geeks offer expert email support and solutions tailored specifically for Auckland businesses. Our professional services ensure your email systems remain robust, secure, and consistently reliable, allowing you to focus on what truly matters—growing your business.

Struggling with persistent email problems? Contact Auckland Geeks today, and let us quickly and expertly resolve your email issues, restoring your business communication smoothly and reliably.