How to send email from specific address when choosing specific contacts?

Same issue here! For years I've been searching for a solution to that.

I agree with @steven-roose, it is not that hard to change the from field.

The problem is: sometimes when I unfortunately forget to do it, I end up sending an email from my personal account to a business colleague or a client, by accident. :/

I have 2 email addresses managed from my Gmail inbox:

• my personal one (me@gmail.com)
• and my work email (me@company.com).

The default "From:" address is my gmail account.

What is ALREADY good: When someone writes an email directly to my work email (in "to:" or "CC:" fields), there is an option in Gmail configuration to automatically select the "From:" address. Works flawlessly.

What is NOT good: When I write an email to a co-worker, I have every time to choose manually my work email in the "From:" field.

What is ALSO NOT good: It also happens when replying to someone that wrote to the customers service email of my company (help@company.com), I have also to choose manually my work email.

What would be a good workaround: A solution to set automatically the "From:" field to "[email protected]" if I set specific recipients ([email protected])

Notes:

1. I've found this UserScript below (whic could be installed with something like TamperMonkey) that was made to auto-select "from" address when you COMPOSE, but it's no longer available (script is no longer maintained): GMail "Send From" Auto Selector

2. Also, there is this suggestion in Gmail Help Forum, but no answers to it.

I assume you're receiving email to only one address, so that both your work and home contacts use the same address to contact you. If so, you cannot automatically set the From field when sending emails.

But if you had two addresses for people contacting you, you could setup default From addresses. When replying to an email, a From address is chosen based on which address was used to receive the message.

Such a scheme means you would need to inform your contacts to use a specific address for work/home related emails. You could use, say [email protected] and [email protected] - anything after the + sign is ignored by Gmail.

Then enter your Gmail settings, and go to the Accounts and import tab. Under Send mail as add new accounts for [email protected] and [email protected]. Take note of the Treat as an alias option to get the behaviour you want.

Also see the official guide to using 'plus' addresses.

I don't think there is. But I don't think either that changing the from field is that hard, is it? It's a simple select box.