For sending emails, custom SMTP now required

thank you so much!!! that was the problem !! I did not have the latest version !! I thought the updates were done automatically on the desktop version … thanks again to you for help! have a good day:souriant:

Hi, I am gmail and putting all my settings in but getting this response

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Must issue a STARTTLS command first. 4sm4584666pfc.92 - gsmtp

No idea what this means I need to do.


Did you read this Guide: And did you follow the link it contains to the Gmail instructions?


When I try and click on the generate password it says my account does not have access to this

Surely it should not be this hard.

@janinastoolbox are you using plain Gmail account or do you use Google Apps / Google G Suite mailbox?

The instructions are for plain Gmail accounts.

For Google G Suite mailboxes, there is a generic guide here:

Plain Gmail

I did not do anything but just tried again and it worked, maybe it took a while to rejig. yay!!!

Hi I have an office 365 email account with a license that i would like to use given the current situation however i keep geting the follow message please advise.

“The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM []”

@Shevvon_Ramroop, did you read and follow the Guide and the link it contains to Office 365 instructions:

@Shevvon_Ramroop the error would indicate you either didn’t select port 587 or entered incorrect username/password in Email Settings form.

Hi, I’m useless with this sort of thing so I apologise in advance but I’ve attempted to follow the steps to create custom SMTP for my google account however at STEP 2 there is no option to turn on the less secure app access. It simply says ‘this setting is managed by your domain administrator’. Any advice on what I should next?
It does say that if using 2-step verification then skip this step and move to step 3. I don’t currently have 2-step verification activated but I can set it up if this will allow me to generate app password as per Step 3? Should I look at doing this or am I better served to find a way to turn on less secure app access? Many thanks

@StefanD the guide is for standalone Gmail accounts.

Are you using Google G Suite? If that’s the case, then this guide is for you:

Great, thank you. I’ve requested to allow users to manage access to less secure apps but this can take 24 hours to activate. I’ll see how I go tomorrow. Cheers

Hi so I did follow the instructions and I am using the port 587, it might have been that I did not enter the right password. After ensuring that I am using the right password this is what I am receiving;

“The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM []”

The only thing I have not done was update to the latest version as I have purchased the server license around 2017. So I am not sure on how to do an update.


Can you please remove port 25 as an option from manager. You should never ever setup a client with port 25. That port is now regarded as soley for communication between mail servers not between client and mail server! You are more likely to end up in the spam folder if you use port 25 and a dynamic IP address!

In addition, requiring sender authentication and encrypting your transmission (i.e. using port 465 or 587) is becoming a mandatory requirement otherwise your email is likely to end up in the spam folder or not delivered at all.

There are only two recommended ports to use now and that is port 465 and port 587.

Port 465 actually uses tls even though most email clients have an ssl tick box. This is a legacy naming strategy to indiate that the email connection is encrypted. SSL3 which is the last SSL version has been deprecated for nearly two decades! I use port 465 but I am only using tls 1.2 as the protocol I can assure you!

I fully understand why people are confused. The ssl setting in most email clients has nothing to do with ssl or tls protocol. It is simply indicating that you want to encrypt the communication. It is very confusing to be told to tick ssl to use tls! But a lot of clients are still putting ssl as the port option even though it’s not actually ssl anymore!

For Manager I would recommend that you only have port 587 as this is technically the only supported directive although in my personal opinion I believe that port 465 is actually more secure as it’s encrypted end to end whereas starttls actually starts off unecrypted and then is upgraded to an encrypted connection. But the first hello is unencrypted.

Port 25 should be removed - its meant for mail server to mail server communication now. Originally it was supported for client to mail server communication but it is no longer acceptable to use that port anymore.

Configure manager to require starttls and to require sender authentication and then you have a fairly secure setup.

In addition, the username should be your email address, not the first part before the @ bit.The standard for logging onto almost all email web browsers is to put your full email addres in.

Users need to use a port supported by their mail server.
I fully appreciate 587 is best but when that is not offered having other options is valuable, and having and order of preference would be useful. Port 25 is used while within many ISP network so authorised by the physical connection being used / modem registration.

Many ISP in a large group of Australian ISP do not support 587, only offering 465
I can confirm both Internode and Adam offer port 25 only for on net email sending and only port 465 for secure roaming email sending. Port 587 can not be enabled (I contacted support)

As for security issues, these were important when a shared Manager STMP server was used. Now users are configuring individual STMP access, it is an individual problem / compromise only.

please help

Have you looked in the forum smtp category and followed the procedure in this post