Why are HelpScout emails not getting replies and potentially going to spam?

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
12Marketer 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.

February 2024 - 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.

May 2023 - SuperOffice
Marketer view

Marketer from Email Geeks suggests reaching out to HelpScout for insight on delivery and deliverability. Recommends inbox testing, reputation review, and quality of customers review.

December 2024 - Email Geeks
Marketer view

Email marketer from GMass explains that a lack of personalization can make emails feel generic and less engaging, potentially leading recipients to ignore or mark them as spam. Recommends using personalized subject lines and content.

January 2024 - GMass
Marketer view

Marketer from Email Geeks suggests there are multiple issues, including content and authentication problems when using a third-party platform like HelpScout. Asks if authentication is properly set up.

December 2021 - Email Geeks
Marketer view

Email marketer from MailerLite Blog explains that sending to unengaged or old email lists can harm your sender reputation and lead to spam filters. Advises regularly cleaning your email list to remove inactive subscribers.

April 2022 - MailerLite Blog
Marketer view

Email marketer from Talking Shrimp explains that boring subject lines are a common reason for low engagement. Suggests using more creative and compelling subject lines to grab attention.

November 2022 - Talking Shrimp
Marketer view

Email marketer from EmailToolTester explains choosing the right email marketing software with good deliverability features is key. They mention Sendinblue as a solid option.

April 2021 - EmailToolTester
Marketer view

Email marketer from Reddit user on r/emailmarketing responds that sometimes the frequency of emails can put off potential clients and they mark as spam because they signed up for 1 email and not more than that per month.

September 2022 - Reddit
Marketer view

Email marketer from Neil Patel explains that a poor sender reputation significantly impacts email deliverability. Suggests improving sender reputation by authenticating emails, warming up IPs, and consistently sending valuable content.

March 2022 - Neil Patel
Marketer view

Email marketer from Litmus explains that emails not optimized for mobile devices can lead to poor user experience and low engagement, potentially resulting in recipients ignoring or deleting the emails. Recommends ensuring emails are mobile-friendly.

March 2024 - Litmus
Marketer view

Email marketer from Sender explains warming up IP helps establish a good sending reputation with ISPs and mailbox providers. This involves gradually increasing sending volume to prove legitimacy.

July 2021 - Sender.net

What the experts say
5Expert 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.

April 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.

February 2024 - Word to the Wise
Expert view

Expert from Email Geeks suggests that being on a shared IP could cause problematic IP/domain reputation. It's possible that Help Scout uses a shared domain for SPF and DKIM.

May 2024 - Email Geeks
Expert view

Expert from Email Geeks provided an authentication summary: Return-Path and 822.From are both help@segmetrics.io. SPF passes. DKIM fails. DMARC p=none passes based on SPF. It’s being sent with BODY=8BITMIME.

March 2024 - Email Geeks
Expert view

Expert from Spam Resource explains that decreasing engagement metrics (opens, clicks) are increasingly being used by mailbox providers to determine spam placement. Lack of recipient interaction can negatively impact deliverability.

July 2022 - Spam Resource

What the documentation says
5Technical 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.

March 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.

September 2024 - SparkPost
Technical article

Documentation from Microsoft Support explains that emails can land in junk folders if they are sent from dynamic IPs, have missing or invalid headers, or trigger spam filters due to content or formatting issues.

September 2024 - Microsoft Support
Technical article

Documentation from Dmarc.org explains that not implementing DMARC, or not properly monitoring DMARC reports, makes it difficult to identify and address deliverability issues related to email authentication.

January 2022 - Dmarc.org
Technical article

Documentation from RFC answers that DKIM failures can cause deliverability issues. Even if SPF is passing, DKIM failures can lead to emails being flagged as suspicious or ending up in the spam folder.

June 2023 - RFC-Editor