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Why you can’t send an email over VPN and how to fix it

Especially this problem can appear when you use a VPN that is not guaranteed, which doesn’t work properly. There are many options available, but not all of them are going to work the same. If you use the wrong one, that can lead to cuts or failures when sending an email.

What to do to fix it

After explaining the reasons why the error sending an email appears when you connect through a VPN, we are going to talk about what to do to solve it. You’re going to have different options for it, as you will see. Most of them are going to be related to the VPN and how you are going to use it.

Restart the device and mail client

The first and most basic thing is restart both the mail client as well as the device. It is what we usually do whenever something goes wrong and in this case we can also try it. It may be the solution if you can’t send an email and see the error message constantly.

You can try restarting your email client, but if this alone doesn’t fix the problem, you could also try restarting your computer. It may happen that there is a conflict at the software level, a component that has not been closed correctly, etc. By restarting both the system and the app, you can see if it fixes it or not. It is the easiest step.

Change the VPN server

Normally VPNs are going to have different servers to connect us. Some may even have a large number of options and this is very useful in order to choose the best one to achieve maximum speed and avoid any type of cut that may appear. If you are connected to one that is not working properly, it may be the reason for these problems.

Therefore, what you are going to do is simply choose another VPN server and connect. If you can send mail normally, you already know that the problem was with the server. If it happens to you again, you can always change to a different one until you see that no type of error appears.

Use another VPN

One option that you will always have available is use another VPN app. You will find a large number of options available, both free and paid. Our advice when it comes to VPNs is to avoid the free ones, as they can pose a security issue and often don’t work well.

If you see that the VPN you use blocks the sending of emails, you can always use a different program. You must make sure that you use a reliable application, downloaded from official sources and that it works well. Some interesting alternatives are those of NordVPN, ExpressVPN or Surfshark. But there are many more and you will simply have to try the one that works best for you and that best suits what you are looking for.

Prevents you from connecting through the VPN

Some VPNs will allow you to choose which programs are going to connect through them and which ones are not. This is an option that you will have in order to get the email to work correctly if you see that the emails you are trying to send are not being sent and problems appear.

Of course, in case you do this you must take into account that the connection will not be encrypted. You are going to send an email normally, as if you did not have a VPN installed. If, for example, you are connected to a public Wi-Fi network, such as an airport or shopping center, your data could be compromised.

In addition, you can take into account the option of momentarily stop the VPN. This will allow you to send that email and, incidentally, check if the problem is really the VPN or it could be another cause at the system level or the email provider you are using.

Use the e-mail in web version

Normally, the problem sending email with a VPN appears when you use a desktop client installed on the Windows system. So what you’re going to do in this case is simply enter the web version and see if the problem continues in this way or you can send it normally.

Using mail from the application or desktop client has its advantages, but you can also run into certain problems, as is the case that we are dealing with in this article. You will always be able to enter Outlook, Gmail or the one you use directly from its website and try to send a message.

Change the ports used by mail

You’ll need to go into the settings for the email client you’re having trouble with. There you will have to configure the SMTP port that it uses, since by default it uses 25 and that may be the reason why it blocks the shipment as it is considered Spam.

You can exchange it for port 587, which is the one that uses SMTP in SSL/TLS encrypted form. In this way you will avoid using the default port and that can be problematic when using a VPN and email.

Check that your equipment works well

You should not rule out that this problem arises from a failure in the system. For example, that you are using an outdated version or that you have unprotected Windows. That could also lead to problems when using certain programs or processes. You must verify that everything is in order and correct it if necessary.

The first thing is to verify that you have windows updated. To do this you have to go to Start, enter Settings and access Windows Update. There you will see possible new updates that are available for you to add and thus have everything updated correctly.

Update Windows 11

You must also have a good antivirus and scan for potential threats. For example, Microsoft Defender itself is a good option, but so are others such as Avast or Bitdefender. There are many options, both free and paid, that you will be able to use and make sure that the system works correctly.

In short, as you have seen, the error when sending an e-mail when you use a VPN is something that can appear. We have explained some possible solutions that you can put into practice in order to be able to send emails without problems even using this type of tool.

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