Why are my transactional emails from Sendgrid being flagged as spam in Gmail, and how can I fix it?

Email marketer from Email on Acid highlights how email content significantly affects spam filtering. He explains the importance of avoiding spam trigger words, using a proper HTML structure, and testing emails across various email clients and devices to ensure they render correctly and don't trigger spam filters.

Email marketer from Neil Patel explains that avoiding the spam folder involves several key steps: segmenting your email list to send targeted content, personalizing emails to increase engagement, using a recognizable sender name and address, and avoiding spam trigger words in your subject lines and email body.

Email marketer from StackOverflow shares that issues with transactional email deliverability often stem from poor IP reputation or misconfigured DNS settings. He advises checking the IP address against known blacklists, verifying the reverse DNS record, and ensuring that the sending IP is properly warmed up before sending large volumes of email.

Email marketer from Reddit explains that if transactional emails are going to spam, check the DKIM/SPF records of Sendgrid. Make sure your sending domain matches the domain used in your 'From' address, and ensure that the content is clearly transactional and avoids promotional language or excessive links.

Marketer from Email Geeks shares that Gmail provides a reason for filtering emails to the spam folder. The reasons could be due to poor domain reputation or the content of the message being flagged or receiving spam votes from recipients.

Email marketer from Mailjet shares that transactional emails can end up in spam if they lack proper authentication, contain suspicious links, or have content that resembles marketing emails. They recommend using a dedicated IP address for transactional emails, monitoring bounce rates, and ensuring the content is purely transactional and not promotional.

Email marketer from Litmus shares that consistent sending volume and engagement are crucial for maintaining a good sender reputation. They recommend gradually increasing sending volume, monitoring engagement metrics (opens, clicks), and promptly removing inactive subscribers to avoid being flagged as a spammer.

Expert from Email Geeks suggests sending example messages from both Sendgrid and Iterable setups to aboutmy.email to identify differences in how links are wrapped and how authentication is handled. The generic Sendgrid clickthrough link may also be the cause of the issue.

Expert from Spam Resource explains that maintaining a current suppression list is critical for deliverability. This involves promptly removing email addresses of recipients who have unsubscribed or marked emails as spam, this will prevent sending to disengaged or problem users in the future.

Expert from Word to the Wise emphasizes the importance of CAN-SPAM compliance for transactional emails. Even if the primary purpose of the email is transactional, it must still adhere to CAN-SPAM regulations. This includes providing an opt-out mechanism, a valid physical postal address, and clear identification that the message is an advertisement (if applicable).

Expert from Email Geeks shares that Google's "this might be phishing" label may be triggered by the landing page content, particularly if it has minimal text and just a login box. The content of the email can also trigger this warning. It isn't a standard "deliverability" problem so standard deliverability advice may not work. Rethinking the re-engagement campaign from the ground up is recommended and potentially avoid calling it transactional if there is not transaction occurring.

Documentation from DKIM.org explains DKIM authentication allows sending organisation to take responsibility for a message, by attaching a digital signature to it, which email systems can then verify. This ensures the email was indeed sent by the domain it claims to be from and that the message's content wasn't altered during transit.

Documentation from RFC explains SPF prevents sender address forgery. SPF records prevent spammers from forging the 'From' addresses in email, meaning the receiving server can verify that emails claiming to come from a specific domain are sent from IP addresses authorized by that domain's administrator.

Documentation from Google explains that Gmail's spam filtering is influenced by factors like sender reputation, authentication, user complaints, and content. They recommend using Google Postmaster Tools to monitor domain and IP reputation, ensuring proper email authentication (SPF, DKIM, DMARC), and adhering to best practices for sending bulk emails to reduce the likelihood of being marked as spam.

Documentation from Sendgrid explains that to improve email deliverability, ensure proper authentication (SPF, DKIM, DMARC) is set up, maintain a clean mailing list by regularly removing inactive or unsubscribed users, monitor your sender reputation using tools like Google Postmaster Tools, and avoid sudden spikes in email volume.