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Summary

HelpScout emails may not be receiving replies and are potentially landing in spam due to a complex interplay of factors. Authentication issues, particularly DKIM failures and potential misconfigurations like wildcard CNAME records, are major contributors. The shared IP environment of HelpScout may lead to a problematic IP/domain reputation. Sending to unengaged or old email lists, a high bounce rate, and a lack of IP warming all contribute to a poor sender reputation. Additionally, content-related problems, such as unengaging subject lines, a lack of personalization, irrelevant content, and emails not optimized for mobile devices, lead to low engagement and spam reports. Insufficient DMARC implementation and monitoring further complicate identifying and resolving authentication issues. Decreasing engagement metrics are also being used to determine spam placement, and the frequency of emails may be a contributing factor.

Key findings

  • Authentication Failures: DKIM failures, potential misconfigurations (e.g., wildcard CNAME), and lack of proper SPF/DMARC lead to spam filtering.
  • Shared IP Reputation: The shared IP environment of HelpScout can result in a problematic IP/domain reputation.
  • Poor Sender Reputation: Sending to unengaged lists, a high bounce rate, and lack of IP warming negatively impact sender reputation.
  • Content Issues: Unengaging content (subject lines, personalization, relevance), poor mobile optimization, and suspicious content trigger spam filters.
  • DMARC Implementation: Insufficient DMARC implementation and monitoring hinder identification and resolution of authentication issues.
  • Engagement Metrics: Declining engagement metrics (opens, clicks) contribute to spam placement.
  • Email Frequency: The frequency of emails might be too high, causing users to mark them as spam.

Key considerations

  • Review Authentication Setup: Thoroughly review and correct SPF, DKIM, and DMARC setup, addressing any misconfigurations like wildcard CNAME records.
  • Consider Platform Alternatives: Evaluate migrating to Google Workspace or another email platform to improve deliverability.
  • Improve Sender Reputation: Implement IP warming strategies, regularly clean email lists to remove unengaged subscribers, and manage bounce rates.
  • Enhance Email Content: Craft engaging subject lines, personalize email content, ensure relevance to subscribers, and optimize emails for mobile devices.
  • Implement DMARC Monitoring: Implement DMARC and actively monitor DMARC reports to identify and resolve authentication issues promptly.
  • Monitor Engagement: Monitor engagement metrics (opens, clicks, spam complaints) and adjust email strategies accordingly.
  • Email Frequency: Check the emails being sent and consider if the email frequency being sent is too much for the end user.

What email marketers say

12 marketer opinions

HelpScout emails may not be getting replies and could be landing in spam for several reasons. These include deliverability issues with the HelpScout platform itself, potentially resolvable by migrating to Google Workspace. Authentication problems (SPF, DKIM, DMARC) are a significant concern. Poor sender reputation, resulting from sending to unengaged lists or lack of IP warming, also plays a role. Content-related issues like unengaging subject lines, lack of personalization, irrelevant content, and failure to optimize for mobile devices can lead to low engagement and spam reports. Frequency of emails could also be a contributing factor.

Key opinions

  • Authentication: Authentication problems (SPF, DKIM, DMARC) are a significant reason for deliverability issues.
  • Sender Reputation: Poor sender reputation, stemming from sending to unengaged lists and the absence of IP warming, contributes to spam placement.
  • Content Engagement: Unengaging subject lines, lack of personalization, irrelevant content, and poor mobile optimization lead to low engagement and spam reports.
  • Platform Issues: Potential deliverability issues with the HelpScout platform itself are causing issues.
  • Email Frequency: Frequency of emails could be a contributing factor and cause email users to mark as spam.

Key considerations

  • Platform Migration: Consider migrating to Google Workspace for potentially improved deliverability.
  • Authentication Setup: Ensure proper setup and monitoring of SPF, DKIM, and DMARC to authenticate emails.
  • List Hygiene: Regularly clean your email list to remove inactive subscribers and maintain a healthy sender reputation.
  • Content Improvement: Improve email content by crafting engaging subject lines, personalizing messages, sending relevant content, and optimizing for mobile devices.
  • Engagement Monitoring: Monitor email engagement metrics (opens, clicks) and adjust strategies based on recipient behavior.
  • Review Email Frequency: Reduce the email frequency as the user may not of signed up for that many.

Marketer view

Marketer from Email Geeks recommends using Google Workspace for HelpScout, noting it's easy to set up and brands emails as the company's own instead of using Help Scout's servers.

11 Apr 2025 - Email Geeks

Marketer view

Email marketer from SuperOffice explains that sending irrelevant content to subscribers can decrease engagement and increase the likelihood of emails being marked as spam. Advises segmenting your email list to send targeted content.

11 Jan 2024 - SuperOffice

What the experts say

5 expert opinions

HelpScout emails may be experiencing deliverability issues and low engagement due to shared IP reputation problems, potential authentication misconfigurations, and declining engagement metrics. The shared IP environment of HelpScout could lead to a problematic domain and IP reputation. There are potential DKIM authentication failures. The use of wildcard CNAME records might also create authentication vulnerabilities. Declining engagement, such as decreased opens and clicks, negatively affects spam placement.

Key opinions

  • Shared IP Reputation: Being on a shared IP with HelpScout may lead to a problematic IP/domain reputation.
  • DKIM Failures: DKIM authentication failures contribute to deliverability issues, even if SPF is passing.
  • Wildcard CNAME: Wildcard CNAME records might introduce authentication vulnerabilities.
  • Engagement Metrics: Decreasing engagement metrics (opens, clicks) are increasingly used to determine spam placement.

Key considerations

  • Evaluate IP Reputation: Evaluate the IP reputation of HelpScout's shared IPs and consider options to mitigate any negative impact.
  • Review DKIM Configuration: Thoroughly review and correct DKIM configuration to ensure proper authentication.
  • Address CNAME Records: Address any wildcard CNAME records to avoid authentication vulnerabilities.
  • Improve Engagement: Implement strategies to improve email engagement, such as personalized content and targeted campaigns.

Expert view

Expert from Email Geeks said segmetrics.io seems to have a wildcard CNAME which invites authentication issues. They are suspiscious of the authentication setup.

11 Aug 2024 - Email Geeks

Expert view

Expert from Word to the Wise explains that authentication failures, especially DKIM, are a primary reason for deliverability issues. Poorly configured or missing authentication can cause emails to be flagged as spam.

30 Apr 2022 - Word to the Wise

What the documentation says

5 technical articles

HelpScout emails are potentially landing in spam and failing to receive replies due to a combination of technical factors. Key issues include lacking proper email authentication (SPF, DKIM, DMARC), which signals to email providers that the messages may not be legitimate. A high spam complaint rate, sending from dynamic IPs, missing or invalid email headers, and triggering spam filters with problematic content or formatting contribute to deliverability problems. DKIM failures specifically cause deliverability issues even when SPF passes. A high bounce rate damages sender reputation. Insufficient use of DMARC or failing to monitor DMARC reports hinders the ability to identify and fix authentication-related deliverability problems.

Key findings

  • Authentication Issues: Lack of proper email authentication (SPF, DKIM, DMARC) results in emails being marked as spam.
  • Technical Problems: Sending from dynamic IPs, having missing or invalid email headers, and triggering spam filters with content or formatting increase the risk of landing in junk folders.
  • DKIM Failures: DKIM failures lead to deliverability issues, even when SPF passes.
  • Bounce Rate: A high bounce rate negatively impacts sender reputation and deliverability.
  • DMARC Usage: Insufficient DMARC implementation and monitoring complicate identifying and resolving authentication-related deliverability problems.

Key considerations

  • Implement Authentication: Implement and validate proper SPF, DKIM, and DMARC email authentication.
  • Review Technical Configuration: Avoid sending from dynamic IPs, ensure email headers are correct and complete, and optimize content to prevent triggering spam filters.
  • Manage Bounce Rate: Monitor and address bounce rates to maintain a healthy email list.
  • Monitor DMARC Reports: Implement DMARC and actively monitor DMARC reports to identify and resolve authentication problems.

Technical article

Documentation from Google Postmaster Tools explains that emails are often marked as spam if they lack proper authentication (SPF, DKIM, DMARC), have a high spam complaint rate, or contain suspicious content.

28 Dec 2022 - Google Postmaster Tools

Technical article

Documentation from SparkPost explains that a high bounce rate can negatively impact your sender reputation and lead to deliverability issues. Recommends monitoring and addressing bounce rates to maintain a healthy email list.

12 Sep 2021 - SparkPost

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