Why do I get privacy errors when clicking email links from Gmail in Chrome?
Michael Ko
Co-founder & CEO, Suped
Published 30 May 2025
Updated 14 Aug 2025
10 min read
Summary
When clicking email links from Gmail in Chrome, encountering a privacy error, often displayed as "Your connection is not private," is a common issue. This typically signifies that your browser, Chrome, cannot establish a secure connection with the website you are trying to reach. The primary cause for this error is usually related to problems with the website's Secure Sockets Layer (SSL) certificate, which is essential for encrypting data and verifying the site's identity. While it might seem like a Gmail-specific issue, the problem generally lies with the landing page's server configuration, or sometimes with how click-tracking domains are set up in email campaigns.
Key findings
SSL Certificate Issues: The most frequent reason for privacy errors is a problem with the website's SSL certificate. This could mean the certificate is expired, revoked, invalid, or issued for a different domain name.
Untrusted Root: Chrome may not trust the Certificate Authority (CA) that issued the SSL certificate, leading to a privacy warning. This is rare for well-known CAs but can occur with self-signed certificates or less common ones.
Domain Mismatch: A common scenario involves a mismatch between the domain in the URL and the domain listed on the SSL certificate. This often happens with email tracking domains or subdomains not properly covered by the certificate.
HSTS Policies: HTTP Strict Transport Security (HSTS) policies can force a browser to always use HTTPS, even if the link in the email is HTTP. If the HTTPS version has an invalid certificate, an error will occur.
Browser Cache: Sometimes, outdated browser cache or cookies can interfere with certificate validation, causing false positives. Clearing these can often resolve transient issues.
Key considerations
Check Certificate Validity: Ensure the SSL certificate for the landing page, and any intermediary tracking domains, is valid, unexpired, and correctly configured. Incorrect configuration can sometimes lead to issues like problems with HTTPS/SSL for email links.
Inspect Tracking Domains: If you use a third-party email service provider (ESP) for click tracking, verify that their tracking domain has a valid SSL certificate that matches the domain they are using for redirects. This is crucial for overall email deliverability.
Verify HTTPS Redirects: Confirm that all your landing pages are properly configured to use HTTPS and that any HTTP links automatically redirect to their secure counterparts. Incorrect redirects can confuse browsers.
Browser Troubleshooting: Advise users to clear their browser's cache and cookies, try an incognito window, or even temporarily disable certain browser extensions that might be interfering. For a general guide on resolving these issues, refer to resources like Kinsta's article on fixing connection errors.
What email marketers say
Email marketers often encounter privacy errors when their subscribers click links from Gmail in Chrome. These issues are frustrating because they can severely impact campaign performance and user trust. Many marketers find that the problem isn't directly with Gmail or Chrome's core functionality, but rather with the SSL configuration of the destination website or any intermediate click-tracking domains.
Key opinions
Tracking Domain Impact: Many marketers report that privacy errors often stem from issues with their email service provider's (ESP) click-tracking domain, especially if it's not properly secured with a valid SSL certificate matching their sending domain. If this is not configured correctly, it could affect broader sender reputation.
HTTPS Requirement: Marketers emphasize the critical need for all linked pages to be served over HTTPS. Chrome and other modern browsers are increasingly strict about secure connections, flagging any HTTP pages or pages with invalid SSL certificates.
Certificate Mismatch: A common observation is that the problem occurs due to a name mismatch on the SSL certificate, where the certificate is issued for a different domain than the one being accessed, particularly when third-party services are involved.
Sudden Appearance: Some marketers note that these errors can appear suddenly, sometimes after recent changes to domain verification (e.g., for Postmaster Tools) or changes to their email infrastructure, even if the certificate itself hasn't expired.
Key considerations
SSL for Tracking Domains: Always ensure your dedicated tracking domains (if used) have their own valid SSL certificates configured correctly. These are often overlooked but are critical points of failure.
Regular Audits: Periodically audit all domains and subdomains used in your email links, including landing pages and image hosts, to ensure their SSL certificates are current and correctly installed. This can also help prevent issues like phishing warnings in Gmail.
Review ESP Settings: If using an ESP, review their documentation or support channels regarding SSL for tracking links. Some ESPs provide options for custom SSL certificates on tracking domains.
Client-Side Checks: While the server-side is key, also consider browser-specific factors. Inform subscribers that clearing browser data or trying another browser can sometimes resolve a persistent Chrome privacy error.
Marketer view
Marketer from Email Geeks indicates that they are encountering a privacy error when clicking links from the Gmail app to Chrome. They inquire whether a disconnect between the sender domain and the site URL could be the cause.
25 Oct 2019 - Email Geeks
Marketer view
Marketer from Email Geeks observed that if the issue affects all links in the email, including those to external sites like YouTube, it suggests the problem is likely with the sender's domain or an intermediary element rather than the destination site itself.
25 Oct 2019 - Email Geeks
What the experts say
Email deliverability experts highlight that privacy errors encountered when clicking email links are fundamentally a web security issue, not solely an email one. These experts stress the importance of a robust SSL/TLS implementation across all domains and subdomains involved in the email click path, including marketing automation platforms and third-party tracking services. The integrity of the certificate chain and domain validation are paramount for preventing such errors.
Key opinions
Certificate Chain: Experts emphasize that the entire certificate chain (root, intermediate, and end-entity certificates) must be valid and correctly installed. A broken chain can lead to untrusted connection warnings, even if the primary certificate appears fine.
Subdomain Security: It is common for email tracking to use subdomains. Experts advise ensuring these subdomains are covered by a wildcard SSL certificate or have their own specific certificates to prevent domain mismatch errors.
HTTP vs. HTTPS: Experts confirm that browsers like Chrome will increasingly flag or block content delivered over HTTP, pushing for a complete transition to HTTPS. Mixed content (HTTP assets on an HTTPS page) can also trigger warnings.
Redirect Issues: Misconfigured redirects, especially from HTTP to HTTPS, can cause problems. If the initial HTTP request is redirected to an HTTPS URL with an invalid certificate, the error will still appear.
Key considerations
Proactive Monitoring: Implement continuous monitoring for SSL certificate expiration and validity for all domains used in email links. Automated alerts can prevent sudden disruptions.
ESP Collaboration: Work closely with your ESP to ensure their tracking domains are fully SSL-enabled and correctly configured to align with your brand's domain. In some cases, a reverse proxy setup can provide more control over the SSL certificate used for tracking.
DMARC Alignment: While not directly an SSL issue, ensuring proper DMARC alignment for your sending domains can indirectly build overall domain trust with ISPs, potentially reducing suspicion in related areas like link security. Proper authentication contributes to a strong domain reputation.
Stay Updated: Keep abreast of browser security updates and best practices for web certificates. Information from resources like Spam Resource can provide valuable insights into industry trends affecting email and web security.
Expert view
Expert from Email Geeks states that Chrome often displays a privacy error when it determines that the SSL certificate presented by the landing page is not trusted. This indicates a fundamental issue with the certificate's authenticity or validity from Chrome's perspective.
25 Oct 2019 - Email Geeks
Expert view
Expert from Email Geeks suggests that if all links in an email are triggering a privacy error, the issue is likely rooted in the link tracking domain used by the sender. This implies a systemic problem with how links are being processed or redirected securely.
25 Oct 2019 - Email Geeks
What the documentation says
Official browser and web security documentation consistently states that privacy errors, such as "Your connection is not private," are a direct result of a browser's inability to securely verify the identity of a website or its secure connection. These warnings are critical security mechanisms designed to protect users from potential man-in-the-middle attacks, phishing attempts, or data interception. The documentation points to fundamental issues with SSL/TLS certificates and their configuration as the root cause.
Key findings
SSL/TLS Certificate Validity: Browser documentation confirms that an expired, revoked, or otherwise invalid SSL/TLS certificate is the primary trigger for privacy errors. Certificates must be current and correctly issued.
Certificate Name Mismatch: If the domain name in the URL does not match the domain name (or a wildcard) on the SSL certificate, browsers will issue a warning. This is a common problem with poorly configured subdomains or tracking links.
Untrusted Certificate Authority: Documentation specifies that browsers only trust certificates issued by CAs that are included in their internal trust store. If a certificate is from an unknown or untrusted CA, a privacy error occurs.
Insecure Protocols: Modern browsers deprecated older, insecure TLS versions (e.g., TLS 1.0, 1.1) and insecure cipher suites. Websites using these outdated configurations will trigger privacy errors.
Key considerations
Implement Valid SSL: Ensure all web properties, especially those linked from emails, have valid, unexpired SSL/TLS certificates from trusted Certificate Authorities.
Correct Certificate Installation: Verify that certificates are installed correctly, including any necessary intermediate certificates, to complete the chain of trust.
Match Domains: Always ensure the domain in the URL exactly matches the domain (or is covered by a wildcard) on the SSL certificate. This is particularly important for tracking links or subdomains.
Use HTTPS Everywhere: Configure servers to automatically redirect all HTTP traffic to HTTPS, and avoid serving any content (images, scripts) over HTTP on an HTTPS page (mixed content).
Technical article
Documentation from Kinsta explains that the "your connection is not private" error primarily arises when your browser fails to verify a Secure Sockets Layer (SSL) certificate. This verification is crucial for establishing a secure and trusted connection.
10 Apr 2024 - Kinsta
Technical article
Documentation from Avast states that "Your connection is not private" error messages typically indicate that a website's SSL certificate has expired, cannot be authenticated, or is entirely missing. These are fundamental issues preventing a secure connection.
