The new SMTP integration is a step BACKWARDS

With the new SMTP integration, there’s no way to send a single email to multiple recipients anymore. Targeting multiple notify entities on smtp.send_message doesn’t produce one message with everyone in To:, it fires a separate individual send per entity. Each recipient sees themselves as the only one on the email, which breaks reply-all and hides who else the report/notification went to.

How it used to work: the legacy notify: platform: smtp YAML config accepted an arbitrary target: list of raw addresses, and HA built one message with all of them in the To: header.

How it works now: each SMTP recipient you add becomes its own fixed-address notify entity. When an automation targets several of those entities in one smtp.send_message call, Home Assistant doesn’t merge them. It dispatches the action once per targeted entity, each an independent send with only that one address in To:. There’s also no cc or bcc field on the action to work around it.

This is a genuine capability regression, not just a config migration. Anyone sending a shared household/family report, a team notification, or anything meant to be visible to a group loses that entirely.

A related thread touches on the same symptom: How to send SMTP to multiple email address now?

I didn’t find an open GitHub issue specifically covering this (checked the integration: smtp label). Is anyone aware of one, or should this get filed? Curious how others are working around it in the meantime. The only option I’ve found is routing through an external mailing-list alias (Google Group, etc.) and registering that as the sole recipient, which puts the fan-out outside HA entirely.

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I think the answer to this is almost always “yes”.

If there is another one already then let them sort that out.

I don’t use the smtp integration (thankfully) but it’s just generic advice.

YES (SMTP integration sends separate emails when multiple recipients are configured · Issue #181046 · home-assistant/core · GitHub)
There is also separate somewhat related issue: impossible now to send to an email address not set up as an entity -
SMTP feature regression - no longer able to provide any email · Issue #178359 · home-assistant/core · GitHub

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