How to Fix Email Sending Issues in Gsuite and Gmail (2024 Guide)

Some time ago, I wrote a post providing a solution to another Google My Business error “Solution to “Cannot access this website” in Google Business“. Today I describe a problem and its solution that has worked for me with several Gmail accounts.

Solution to Email Sending Issues in Gsuite and Gmail (Updated 2024)

If you have a Gsuite account linked with other Gmail accounts, you may have encountered this issue. In my case, under Settings/Accounts/Send As and Check mail from other accounts, it is very useful to have my main emails on the same platform without switching between accounts:

As you can see, I have many accounts, and all were working fine until today, but for some reason the Gmail accounts stopped working. I received a bounced email like this:

This is the response from the remote server:
534 5.7.9 Application-specific password required. Learn more at https://support.google.com/mail/?p=InvalidSecondFactor i5sm2454861qtw.97 – gsmtp
And when I went to check the settings, it gave me an error indicating that the password was incorrect.

Authentication failed. Check your username/password and access for less secure apps for webalicanteinformatica.
The server returned an error: “535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/?p=BadCredentials w134sm36009qkb.47 – gsmtp, code: 535”
The password was not the issue but THE TWO-STEP VERIFICATION of Gmail, and simply deactivating it, everything was resolved!

Deactivate Two-Step Verification

Two-Step Verification is a security measure that adds an extra layer of protection to your account. However, it can cause issues when trying to send emails from linked Gmail accounts. Here’s how to temporarily deactivate it to resolve these issues:

Follow these steps to deactivate Two-Step Verification:

1. Log in to your Google account.
2. Go to the Google security checkup.
3. In the “Signing in to Google” section, select “Two-Step Verification”.
4. You may be asked to sign in again.
5. Click “Turn off” and follow the on-screen instructions to complete the process.

Note that by deactivating Two-Step Verification, your account will be less secure. It is advisable to seek alternative solutions to avoid deactivating it, such as generating application-specific passwords. More information on Two-Step Verification: https://www.google.com/landing/2step/?hl=en
Let’s hope that Google fixes this issue and we can have Two-Step Verification back as before since this problem is very new, and my account has had this same configuration for years.

Generating Application-Specific Passwords

Generating application-specific passwords is a secure way to allow certain applications or devices to access your Google account without disabling two-step verification. Here’s how to do it:

Steps to Generate Application-Specific Passwords

1. Log in to your Google account and go to the Security section of your account.
2. In the “Signing in to Google” section, select “App passwords”.
3. You may be asked to sign in again to confirm your identity.
4. Select the application and device for which you need the password.
5. Click “Generate”.
6. A specific password for the application will be generated. Use this password instead of your regular Google password when setting up the application or device.

It is important to keep these application-specific passwords secure and only use them for the designated devices or applications. Here are some additional tips for managing them:

• Store passwords securely: Use a password manager to store and manage these passwords securely.
• Revoke passwords when no longer needed: If you stop using an application or device, revoke the specific password for that application from the same section where you generated it.
• Monitor access to your account: Regularly review the activity on your Google account to ensure that only authorized devices and applications have access.

Extra Solution: Gsuite – Less Secure Apps

In addition to temporarily disabling Two-Step Verification, another solution to resolve email sending issues is to allow access to less secure apps. This setting is especially useful if you use applications or devices that do not support Two-Step Verification.

Follow these steps to allow access to less secure apps in Gsuite:

1. Log in to your Gsuite admin console.
2. Go to the Security section.
3. Select Control access to less secure apps.
4. Enable the option that allows users to manage their access to less secure apps.
5. Once enabled, users can allow access to less secure apps from their own Google accounts.

Note that allowing access to less secure apps may increase the security risk to your account. Ensure that only trusted applications and devices have access to your Google account.
For individual users who need to enable this option, follow these steps:

1. Log in to your Google account.
2. Go to the Security page of your account.
3. In the Less secure app access section, click “Turn on access (not recommended)”.
4. Confirm your choice in the pop-up window.

More information on access to less secure apps: Access to less secure apps
Implementing this solution can resolve email sending issues, but it is always advisable to review and use more secure methods like generating application-specific passwords whenever possible.

Importance of Two-Step Verification

Two-Step Verification is an additional security measure that helps protect your account from unauthorized access. While disabling it can temporarily resolve email sending issues, it is recommended to keep it enabled and seek other more secure solutions.
One option is to generate application-specific passwords, which allow certain applications or devices to access your Google account without needing to disable two-step verification. This keeps your account protected while solving the access issue.

Email Authentication Setup

To ensure correct email delivery and improve the security of your domain, it is essential to properly set up email authentication. This includes SPF, DKIM, and DMARC records.

1. SPF (Sender Policy Framework)

The SPF record helps prevent spammers from sending emails on behalf of your domain. Follow these steps to set it up:

1. Access your domain’s DNS settings.
2. Add a new TXT record with the value: v=spf1 include:_spf.google.com ~all.
3. Save the changes and verify that the record has propagated correctly.

2. DKIM (DomainKeys Identified Mail)

DKIM adds a digital signature to your emails, ensuring they haven’t been altered during transit. Set it up as follows:

1. In the Google Workspace admin console, go to Apps > Google Workspace > Gmail > Advanced settings.
2. In the Email authentication section, click Generate new record.
3. Follow the instructions to add the DKIM record to your DNS settings.

3. DMARC (Domain-based Message Authentication, Reporting & Conformance)

DMARC tells email servers how to handle messages that fail SPF or DKIM checks. Here’s how to set it up:

1. Add a TXT record in your DNS settings with the value: v=DMARC1; p=none; rua=mailto:[email protected].
2. Review and adjust the DMARC policy according to your needs (e.g., p=quarantine or p=reject).

Implementing and maintaining these records will help protect your domain against unauthorized use and improve your email delivery rate.

Tips for Managing Multiple Email Accounts

Managing multiple email accounts can be challenging, especially when using different email providers. Here are some practical tips to keep your accounts organized and ensure they all work correctly:

1. Use a Centralized Email Client

A centralized email client like Microsoft Outlook or Thunderbird can make managing multiple email accounts easier. These applications allow you to add multiple accounts and manage them from a single interface. This not only simplifies access to your emails but also helps you keep all your communications in one place.

2. Set Up Rules and Filters

Set up rules and filters to automatically organize your incoming emails. For example, you can create filters to move emails from different accounts to specific folders or label them according to their priority. This can help you keep your inbox tidy and prioritize important emails without manually sorting through each message.

3. Keep Your Login Information Secure

Use a password manager to store and manage your passwords securely. This makes it easier to access your accounts without having to remember multiple passwords. Additionally, a password manager can generate secure and unique passwords for each of your accounts, significantly enhancing security.

4. Perform Regular Audits

Regularly review the settings of your email accounts to ensure everything is up-to-date and functioning correctly. This includes checking security settings, application-specific passwords, and ensuring there are no unauthorized accesses. Regular audits help you identify and fix issues before they impact your workflow.

5. Sync Your Calendar and Contacts

In addition to email, sync your calendars and contacts across all your accounts. This will allow you to manage your appointments and contacts from a single platform, avoiding duplications and ensuring you always have up-to-date information.

6. Use Mobile Apps

Install mobile email apps that support multiple accounts. Apps like Gmail, Outlook, and other email clients allow you to manage multiple accounts from your mobile device, making it easier to access your emails anytime, anywhere.
By following these tips, you can keep your email accounts organized and functional, improving your productivity and ensuring you don’t miss any important messages.

Alternatives to Disabling Two-Step Verification

While disabling two-step verification can resolve email sending issues, it is preferable to keep this security measure enabled and explore other more secure solutions. Here are some alternatives:

1. Use Application-Specific Passwords

Generating application-specific passwords is a secure alternative that allows you to keep two-step verification enabled. These passwords are generated for specific applications or devices that do not support two-step verification, allowing them to access your Google account without compromising security.

1. Log in to your Google account and go to the Security section of your account.
2. In the “Signing in to Google” section, select “App passwords”.
3. You may be asked to sign in again to confirm your identity.
4. Select the application and device for which you need the password.
5. Click “Generate”.
6. Use this specific password for the application instead of your regular Google password when setting up the application or device.

2. Update Applications and Services

Make sure all applications and services you use to manage your emails are updated to the latest version. Updates often include security and compatibility improvements that can resolve connection and email sending issues.

3. Consult Technical Support

If you continue to have problems, consider contacting Google support or the support team for the email application you are using. They can offer specific solutions for your situation. Be sure to provide them with complete details about the problem and the solutions you have already tried to implement.
Google support can be contacted through their Help Center, where you will find guides and contact options for personalized assistance.

4. Use Alternative Email Clients

Consider using email clients that support two-step verification and offer support for multiple accounts. Applications like Microsoft Outlook, Mozilla Thunderbird, and other advanced clients can provide more robust and secure solutions for managing multiple email accounts.
Implementing these alternatives will allow you to keep two-step verification enabled, ensuring maximum security for your Google account while solving email sending issues.

My Opinion as a Digital Marketing Expert

Managing multiple email accounts from one platform can present challenges, especially when configuration and authentication issues arise. However, with the right solutions, such as temporarily disabling two-step verification and using application-specific passwords, it is possible to maintain an efficient and secure workflow.
I hope this guide has been helpful. If you have more questions or need additional assistance, do not hesitate to leave a comment or visit my digital marketing blog for more resources on SEO, digital marketing, and technology.
If you are interested in staying updated on SEO, I recommend this article:

Study of the Best SEO Tools. Search and Trends Analysis

Best regards, and if you found this interesting, feel free to check out the rest of the blog where I cover various topics like SEO, web design, neuromarketing, and more.

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