Outlook not using correct account in From:

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This has been an ongoing problem.

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I have a main 3rd party account. This account also has 2 aliases. I have the main account and the two aliases set up as accounts in Outlook, with all 3 using the same incoming and outgoing server info. Of course, both aliases show all the same mail as the main account. I did this so that they would be available for correction in the From field.

When I am replying to an email sent to aliase1, the From field shows the Main address, not the aliase1 address. I have to change it manually. Email properties show the email as “delivered to aliase1, resolved to Main”.

This issue tends to compromise my use of aliases, since I may forget to check and change the From field before sending the reply.

1. is there a way to get Outlook to auto automatically show the ‘delivered to’ address in the From field?

if not, 2. If I could convince the 3rd party provider to allow Outlook log in to servers using alias addresses , would this fix the problem? iow, is Outlook getting the From address from the account outgoing server address?  Or does Outlook get info for the From: field from the resolved to:  info?  How does Outlook determine what address to use in the From: field?

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The mail client puts the “from” address in – it generally uses the default email account as the account for both new mail and replies, but it is client dependent.
I don’t know it Outlook allows you to change this.

cheers, Paul

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I have a number of email addresses.  Outlook is using whatever address the email arrived under as the reply From.  Of course all those other email addresses also use that address in the accompanying login for those accounts.

I am wondering, if the email company, Fastmail, allowed login from the aliases, so that I could include the alias address in the smtp login, rather than the main account address, this would fix the problem?  or is Outlook taking the From account from elsewhere?  eg, from the “resolved to…” in the email header?

Do you use Outlook? or any email client?  Am i one of a few people, outside of corporations to be using Outlook? This seems like such a ridiculous issue to be having.

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The current versions of Outlook (2016/2019/365) default to using the primary email address of the current inbox (1) or in replies the address to which that email was sent.

1) If you have multiple email accounts going to separate inboxes as shown in the left folder view, whichever inbox is currently in focus will dictate which outgoing email address will be selected when you click “new Email.” This is by design.

In the case where you have aliases setup on the same primary account, with one Inbox folder, then no – there is no way to tell Outlook to use a specific alias if that alias is NOT the primary account.

Likewise, there is no way to add a column that shows the sending alias, its limited to the primary account.

What works better is to create separate Inboxes as PST’s and create rules in Outlook that will sort incoming by alias into their proper Inbox. It’s still kludgy, but then so is the use of multiple aliases (as opposed to actual email accounts) for one account.

~ Group "Weekend" ~

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I just tried setting up a POP account for one alias.  I moved an email that was addressed to the alias to that pst folder and tried replying to it.  Still showed as replying From the Main account. While it is possible that I got some detail wrong in the POP setup, I am thinking that Outlook is getting the From address from something in the email header.  This makes sense to me since a number of different accounts wind up in the same POP pst and those all get replied From  the correct account.

I am guessing that the line in the header about the Alias being ‘resolved to’ Main is the culprit.  If this is the case, then there is likely nothing I can ask Fastmail to change that would fix this. Also, they saythat they don’t allow login from aliases because some users want to use aliases as security against account hacking.

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Fastmail suggests that I use their web mail instead, or a different email client.  I have looked at Thunderbird, and Evolution, but it seemed like they couldn’t hold all the address book data that I have in Outlook.  Multiple addresses (Home, Work, Other),  the different phone #’s, personal details and notes about the contact, web site address, etc.

Possible that I missed something, or there is an addin, but I didn’t see it.

Or maybe Thunderbird or Evolution would have the same issue.

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Yes, Outlook does the sender address handling sort of weirdly unless you configure it on your outgoing Exchange server just right. And if you don’t have an Exchange server, well, Microsoft sells those too…

So yes, it does seem to be on purpose.

astro46 wrote:

I have looked at Thunderbird, and Evolution, but it seemed like they couldn’t hold all the address book data that I have in Outlook. Multiple addresses (Home, Work, Other), the different phone #’s, personal details and notes about the contact, web site address, etc.

Hm, I haven’t had problems syncing those to server with Thunderbird. Yes, possibly needs an addin or even several, based on which kind of server it is.

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mn– wrote:

Hm, I haven’t had problems syncing those to server with Thunderbird. Yes, possibly needs an addin or even several, based on which kind of server it is.

sync to server?   I am referring to importing the data from Outlook to Thunderbird.

Am I wrong to assume that Thunderbird would handle the From issue better than Outlook?

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astro46 wrote:

Am I wrong to assume that Thunderbird would handle the From issue better than Outlook?

Yeah, if you have multiple aliases defined you can choose any of them as the sender, and you can even just edit the From header before sending (but if you do that, by default it nags you that the some servers don’t allow freeform modified From lines).

astro46 wrote:

sync to server? I am referring to importing the data from Outlook to Thunderbird.

Meh. Last time I tried (2018, 365 E3 Outlook), Outlook couldn’t correctly handle a direct export/import from itself and back even (yes, same instance and profile), unless you’d originally stored everything in 7-bit US-ASCII… yes, over here a difference between a and ä in an address can mean a longish drive.

Server side export/import has been more reliable.

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[astro46]

mn– wrote:

Yeah, if you have multiple aliases defined you can choose any of them as the sender, and you can even just edit the From header before sending (but if you do that, by default it nags you that the some servers don’t allow freeform modified From lines).

I can change the From field in a reply in Outlook, with no nagging.  If I will have to manually do this in Thunderbird also, and get nagged, there is nothing to be gained by moving.  I am looking for the reply to default to showing the original To: account in the reply From:

mn– wrote:

Meh. Last time I tried (2018, 365 E3 Outlook), Outlook couldn’t correctly handle a direct export/import from itself and back even (yes, same instance and profile), unless you’d originally stored everything in 7-bit US-ASCII… yes, over here a difference between a and ä in an address can mean a longish drive.

Yes, exporting data to another program has always been a quagmire, and I wouldn’t be looking forward to doing it Outlook to Thunderbird.   I use Exchange to deal with keeping my Outlook calendar in sync with Iphone calender,  and that would be another issue in dealing with dropping Outlook.

All in all, I am feeling less and less incentive to attempt it.

• This reply was modified 4 years, 10 months ago by astro46.

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astro46 wrote:

I can change the From field in a reply in Outlook, with no nagging. If I will have to manually do this in Thunderbird also, and get nagged, there is nothing to be gained by moving. I am looking for the reply to default to showing the original To: account in the reply From:

The nag dialog has a “don’t show again” option.

Also you don’t get it at all if you use one of your known preconfigured aliases, it’s only for ad-hoc edits to the From field in the message writing interface.

astro46 wrote:

Yes, exporting data to another program has always been a quagmire, and I wouldn’t be looking forward to doing it Outlook to Thunderbird. I use Exchange to deal with keeping my Outlook calendar in sync with Iphone calender, and that would be another issue in dealing with dropping Outlook.

Well, if you have an Exchange server (or Exchange Online enabled account), things are much easier already. Thunderbird with the right addins works just fine with Exchange, both calendar and addressbook sync. Also copes with Unicode in addresses and the like if you do it that way.

You could just use both Outlook and Thunderbird for a while. Add a contact in Outlook, sync Outlook with server, then sync Thunderbird with server, and see how the contact looks there…

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I use Thunderbird and Fastmail and I can’t use aliases without setting them up locally – that is too much hassle. I use the web client if I need to use an alias.

cheers, Paul

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Thanks for the comments, suggestions. I will try out thunderbird, see how data transfers, if the email part works better, and how it all syncs with iphone. If it all works out, I won’t be dealing with Outlook any longer.

1 user thanked author for this post.

Elly

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