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Gmail: Be Careful with This Message – Technipages


Gmail may sometimes suggest you should be careful with a particular message. Or it may prompt your recipients to be careful with the emails you sent them. Let’s try to decipher why Gmail advises users to be careful with certain emails.

The main reason why Gmail pops up this alert is that it could not verify the problematic email actually came from the sender’s email address.

However, even email addresses stemming from G-Suite accounts can be flagged as suspicious. Gmail flagging another Gmail account coming within the Google ecosystem can be really confusing. Jump straight to the second and third solutions to learn why that happens.

Unfortunately, there is no specific option to disable Gmail’s warnings and alerts.

How Do I Get Rid of ‘Be Careful with This Message’ in Gmail?

Add the Sender to Contacts

If you’re completely sure the sender is reputable, try adding them to your Contacts list. In this manner, you let Gmail know you trust the sender. Hopefully, Gmail’s security algorithms won’t display similar alerts in the future.

Additionally, if the warning comes with a ‘Looks safe‘ option, you can click on it. Gmail relies on a series of filters to assess the emails you receive. When you mark a sender as safe, you basically tell Gmail the sender is trustworthy.

Check Your Domain SPF Record Settings

Make sure the email server has been authorized under the domain SPF record settings. As a quick reminder, SPF stands for Sender Policy Framework. This is an email authentication method Gmail uses to detect attempts of forging sender addresses.

If the sender uses a third-party email program to send messages through an SMTP server that is not authorized in the domain’s SPF record, Gmail will advise you to be careful with that message.

This often happens when Gmail users login into their accounts via an email software solution. That program actually uses their ISP’s server to send the messages, instead of using Gmail’s server. The problem is there is no specific SPF record authorizing your ISP’s server to send emails on behalf of gmail.com. As a result, the message looks suspicious.

There are two solutions to fix this issue:

  • Send your messages from a browser signed in at mail.google.com.
  • Tweak your email software settings to send via smtp.gmail.com. For more information on using Google’s SMTP servers, see Send emails from a different address or alias.

For additional information, see Ensure mail delivery & prevent spoofing on Google Support.

Authenticating Your Domain via DKIM

Additionally, if you’re using a custom domain, try authenticating your domain via DKIM. Hopefully, this will prevent the alert from popping up.

DKIM stands for DomainKeys Identified Mail. This email security protocol that guarantees messages isn’t altered or edited while they’re in transit from the sender’s server to the recipient’s server.

For more information, see Set up DKIM to prevent email spoofing on Google Support.

Create a Filter for That Sender

If you know and trust the sender, you can create a specific filter to remove the warning from their future messages.

  1. Launch Gmail and open the problematic email.
  2. Click on the three dots to open the menu and select Filter message like this.filter message like this gmail
  3. Click on Create filter.
  4. Check Never send it to Spam. Or create a special category for similar emails.

create email filter gmail

Remove Links from Signature

Try removing all the links from your email signature and check if the error is gone. As a quick reminder, links in the signature block can be flagged as spammy.

Let us know if these solutions helped you eliminate Gmail’s ‘Be Careful With This Message‘ alerts.



This post was written by Madalina Dinita and was first posted to Technipages



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