Why are HelpScout emails not getting replies and potentially going to spam?
Matthew Whittaker
Co-founder & CTO, Suped
Published 18 Apr 2025
Updated 17 Aug 2025
7 min read
It can be incredibly frustrating when your customer support emails, especially those sent via a platform like HelpScout, aren't getting replies or seem to be disappearing into the void. This issue often stems from a combination of technical deliverability problems and content-related factors that impact recipient engagement. When customers report not receiving responses, or when proactive outreach yields no results, it's a clear signal that your emails might be landing in spam folders (or blocklists) or simply being overlooked.
Diagnosing these issues requires a systematic approach, looking beyond just whether the email was 'sent' and delving into how it was received and perceived by the recipient. The challenge for many businesses using third-party customer service platforms is that some aspects of email sending are managed externally, which can complicate troubleshooting. Let's explore the common culprits and how to tackle them.
Technical authentication failures
One of the first suspects in any email delivery issue is the technical setup of your sending domain. While HelpScout often advises on recommended SPF, DKIM, and DMARC configurations, the way these are implemented, especially when using a shared platform, can still lead to problems. Issues like a DKIM signature failing or an SPF record not fully aligning with your sending patterns can severely impact your emails' chances of reaching the inbox.
For support conversations and proactive outreach, where replies are crucial, email authentication is paramount. When your emails don't properly authenticate, mailbox providers are far more likely to flag them as suspicious or outright send them to the spam folder. This is why even if HelpScout states your setup is as recommended, it's essential to verify the actual authentication results for emails sent from the platform.
This involves checking the raw headers of an email sent from HelpScout to a test inbox. Tools for this exist, and they can show you the specific authentication results for SPF, DKIM, and DMARC. If you see a DKIM=fail, even if SPF passes and DMARC is set to p=none, it indicates a problem that needs addressing. You can learn more about DMARC, SPF, and DKIM in our guide.
Checking email headers
When an email seems to be going to spam or not getting replies, checking its full header information is a critical first step. This data provides insights into the email's journey and why it might have been flagged. HelpScout itself provides troubleshooting steps for outbound delivery issues, which often involve examining headers.
Example email headers (simplified)plaintext
Received: from mail.helpscout.net (mail.helpscout.net [198.51.100.1])
by mx.example.com with ESMTP id ABCDEFGH for <recipient@example.com>; Mon, 1 Jan 2024 12:00:00 -0000
Authentication-Results: mx.example.com; spf=pass (sender IP is 198.51.100.1) smtp.mailfrom=helpscout.net;
dkim=fail (body hash did not verify) header.d=yourdomain.com
Received-SPF: Pass (sender IP is 198.51.100.1)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=yourdomain.com; s=helpscout;
h=from:to:subject:mime-version:content-type:content-transfer-encoding:message-id:date;
bh=...
b=...
From: Your Support <help@yourdomain.com>
To: recipient@example.com
Subject: Re: Your support request
Shared IP vs. Own mail server
A key factor in email deliverability is sender reputation. When you use a third-party platform like HelpScout, you might be sending emails from shared IP addresses or domains. If other users on these shared resources engage in practices that harm their sender reputation, it can negatively impact your email delivery as well, even if your own sending practices are impeccable. This is a common challenge with many SaaS providers.
Mailbox providers (like Gmail Outlook, and Yahoo) continuously monitor the reputation of sending IP addresses and domains. If your emails are originating from an IP or domain with a poor reputation (perhaps due to being on a blacklist or blocklist), they are more likely to be sent to spam. This is true even for transactional or support emails, which are generally expected by recipients.
HelpScout's suggestion to switch to your own Google Workspace or Microsoft 365 account for sending is a strong indicator of this. By using your own mail server, you gain direct control over your sender reputation and authentication, rather than sharing it with potentially hundreds or thousands of other HelpScout users. This can significantly improve your domain reputation and overall email deliverability.
Shared IP/domain reputation
When using a shared sending infrastructure, your email reputation is tied to that of other users on the same IPs or domains. A sudden surge of spam or poor sending practices by another user could lead to the shared IP being added to a blacklist (or blocklist), impacting your deliverability.
Risk: Vulnerable to the sending behavior of other HelpScout users, potentially resulting in emails going to spam.
Visibility: Less transparency into the overall health of the shared sending infrastructure.
Dedicated sending via own mail server
By configuring HelpScout to send emails through your own Google Workspace or Microsoft 365 mail server, you gain direct control and responsibility for your sending reputation. Your deliverability performance then depends solely on your practices.
Control: Your deliverability is directly controlled by your sending volume and engagement metrics.
Authentication: Ensures that your emails are properly authenticated with your own domain, improving trust with mailbox providers.
Content and engagement issues
While technical deliverability is crucial, content and engagement also play a significant role in whether your emails get replies. If emails are consistently landing in the inbox but not generating responses, the issue might lie in the email's content, clarity, or its ability to motivate the recipient to act. This is particularly true for proactive outreach, where the recipient isn't necessarily expecting your message.
For customer support emails, while the user expects a reply, poorly structured or unclear responses can still lead to missed communications. Lengthy emails, lack of clear calls to action, or confusing subject lines can result in recipients overlooking or deprioritizing your messages. Remember, even if an email avoids the spam filter, it can still be buried in a busy inbox or simply ignored.
It's also worth considering how mailbox providers categorize your emails. For example, some email providers may categorize certain types of support emails under the Promotions tab or similar, even if they aren't promotional. While this isn't necessarily a spam issue, it can still reduce visibility and reply rates. You can gain more insight into this by understanding why your emails are going to spam in general.
Factor
Impact on replies
Mitigation
Spam folders
Emails are delivered but filtered into the spam or junk folder, making them unseen.
Improve sender reputation and authentication. Check blocklists. Implement DMARC with a stricter policy over time.
Promotional categorization
Emails land in tabs (e.g., Gmail Promotions) that recipients check less frequently.
Optimize content to avoid promotional triggers. Focus on direct, clear subject lines for transactional emails.
Low engagement
Recipients see the email but don't find the content compelling enough to reply.
Refine email copy for clarity, conciseness, and a strong call to action. Personalize messages.
Invalid/inactive addresses
Emails bounce or are silently dropped due to invalid or old recipient addresses.
Regularly clean your contact lists. Implement double opt-in for marketing emails. Learn about silently dropped emails.
Actionable steps to improve
To systematically address these issues, I recommend a multi-pronged approach. First, prioritize moving your HelpScout sending to your own mail server, such as Google Workspace or Microsoft 365. This gives you more control over your email authentication (SPF, DKIM, DMARC) and overall sender reputation. HelpScout provides straightforward guides for this setup, which typically involves adjusting DNS records.
Second, actively monitor your sender reputation. Even after switching to your own server, reputation isn't static. Utilize tools like Google Postmaster Tools to track your domain's health with Gmail and other postmaster tools for Outlook.comand Yahoo Mail. This provides valuable feedback on your spam rates and overall deliverability. Being listed on a blocklist or blacklist is a common reason for deliverability issues, so utilize a blocklist checker regularly.
Finally, don't neglect your content. Review your support email templates and proactive outreach messages. Are they clear, concise, and do they have a single, obvious call to action? Consider A/B testing different subject lines and body copy to see what resonates best with your audience. Sometimes, the problem isn't that the email didn't arrive, but that it arrived and failed to capture the recipient's attention. HelpScout has guides on troubleshooting conversations in 'needs attention' and other related topics, which may offer further insights into engagement.
Summary
Experiencing low reply rates or emails going to spam (or getting blocklisted) when using HelpScout for customer support or outreach can be a multifaceted problem. It's often a blend of technical deliverability challenges and issues with email content or recipient engagement.
By focusing on strong email authentication, optimizing your sender reputation, and crafting engaging, clear content, you can significantly improve the chances of your HelpScout emails landing in the inbox and prompting the desired responses. Consistent monitoring and an iterative approach to testing will be key to long-term success.
Views from the trenches
Best practices
Always check your email headers for authentication results (SPF, DKIM, DMARC) on a regular basis.
Consider configuring HelpScout to send emails through your own Google Workspace or Microsoft 365 mail server.
Proactively monitor your domain and IP reputation using postmaster tools.
Regularly review and refine your email content, subject lines, and calls to action.
Common pitfalls
Assuming deliverability is solely the responsibility of the email service provider you are using.
Ignoring DMARC reports, which can provide critical insights into authentication failures.
Not cleaning your email lists, leading to bounces and engagement issues.
Using generic, unengaging subject lines for crucial support or outreach emails.
Expert tips
Send test emails to various mailbox providers (Gmail, Outlook, Yahoo) to check inbox placement.
Focus on maintaining a positive sender reputation, as it directly impacts delivery.
For proactive outreach, ensure your messages provide clear value and context to the recipient.
Implement feedback loops where possible to understand why recipients might be marking your emails as spam.
Marketer view
Marketer from Email Geeks says that reviewing your domain and IP reputation is a crucial step when diagnosing deliverability issues. It's also important to check the quality of newly acquired customers.
2023-09-06 - Email Geeks
Expert view
Expert from Email Geeks emphasizes the importance of verifying proper email authentication setup, especially when using a third-party platform for sending.
Gmail 
Outlook, and 
Yahoo) continuously monitor the reputation of sending IP addresses and domains. If your emails are originating from an IP or domain with a poor reputation (perhaps due to being on a blacklist or blocklist), they are more likely to be sent to spam. This is true even for transactional or support emails, which are generally expected by recipients.
Outlook.com
