This mail is unauthenticated

[neilmcc]

Hi, having trouble sending emails to gmail accounts from my outlook.com address. It has worked in the past to the same address.
Stupid thing is sending invoices out from Cashbook works.
Are there some easy to understand instructions for me to check why this is happening? I have a look online but got lost on the first accent!!!
Using Outlook 2016 ,I think it is.
Of course, no problem if I use my gmaill account.
Thanks.

Message back to me reads,
     host gmail-smtp-in.l.google.com[74.125.200.27] said:
    550-5.7.26 This mail is unauthenticated, which poses a security risk to the
    550-5.7.26 sender and Gmail users, and has been blocked. The sender must
    550-5.7.26 authenticate with at least one of SPF or DKIM. For this message,
    550-5.7.26 DKIM checks did not pass and SPF check for [outlook.com] did not
    550-5.7.26 pass with ip: [202.137.240.16]. The sender should visit
    550-5.7.26  https://support.google.com/mail/answer/8...entication for
    550 5.7.26 instructions on setting up authentication.
    k71-20020a63844a000000b00553b006cd9fsi3889033pgd.728 - gsmtp (in reply to
    end of DATA command)

[Wainuitech]

Problem "could" actually be outlook 2016. Seen all sorts of problems especially with Gmail when using old Programs, as they are upping their security.

One way to test -- Download and install something newer, suggest eMClient  https://www.emclient.com/    Add in your outlook.com account and try sending a test message to the same address you are currently having problems. If it works then  looks like Outlook  could be the problem. Had MANY customers using older Outlooks or live mail with similar problems.

If EMclient works, there's a free version, from memory you can have 2 accounts, any more you need the paid, you can change the Themes ( to a degree). If outlook is to old and causing problems, two choices, buy a Newer Outlook, or use a free/different Program.

If it still fails on EMClient then its something else.

Edited: Also, since its listing your IP address, if you have a dynamic IP address ( meaning it changes) compared to a Static which is the same all the time, its possible that IP has been black listed for some reason, IF this is the case as soon as your IP changes again things may come right.

[king1]

I think this is because you are sending off your own domain based email and there is no configured SPF record  or domain key setup  in the DNS records - google changed stuff there end (ie the "sender must authenticate with at least one of SPF or DKIM" bit} a while back to require one or the other from senders to gmail.  

You need to get your hosting provider to add an SPF/DKIM records - i've had a few business clients caught out by this

[Wainuitech]

Guess the million $$ Question here is are you using a Domain Name Via Outlook.com, OR just outlook.com within Outlook 2016 ???

[neilmcc]

Guess the million $$ Question here is are you using a Domain Name Via Outlook.com, OR just outlook.com within Outlook 2016 ???

Thanks for your replies.Just using outlook.com with Outlook 2016, if that helps!. If it persists I can use my gmail account to send work certificates to the odd client using gmail. Thanks again. Bit lost with this!

[king1]

something is mixed up here, you say you are sending the mail using you Outlook.com email address?

but the IP address 202.137.240.16 resolves back to NOW New Zealand Ltd. (AS9876) - my isp as it happens...

this tool below identifies the Ip address is associated with smtp.airnet.net.nz, which looks to belong to NowNZ, smtp is an outgoing mail server

https://mxtoolbox.com/SuperTool.aspx?act...n=toolpage

So it looks to Google like you are trying to send your Outlook.com email via the NOW NZ mail server smtp.airnet.net.nz
and the SPF is failing because the Outlook.com SPF record won't include a NOW NZ IP address.

I think I would be looking in you email settings in Outlook 2016 to see what incoming/outgoing mail servers are being used, for Outlook.com emails it would be smtp.office365.com

but clearly this is not the case, as identified in the gmail error, it looks like you could have that as smtp.airnet.net.nz

[king1]

@neilmcc
You don't have any other email address involved in the business/cashbook other than the something@outlook.com email?

[neilmcc]

@neilmcc
You don't have any other email address involved in the business/cashbook other than the something@outlook.com email?

Correct. And yes my internet supplier is NOW.

[Wainuitech]

Best check your email settings, If you are using Outlok.com as your main Email the mail setting should be to them ( automatically and cant be configured) . As if you are trying to go through NOW,  google esp will throw a real hissy fit, as that's relaying, and most wont allow it.

Edited:  ASSUMING you are using Outlook as its meant to be used, as IMAP, you can try deleting the account in outlook 2016 ( on the computer) , re-entering it from fresh. IMAP will automatically put in the correct settings and re-download / sync all mailboxes, contacts etc.

Sure Outlook.com will have all the required certificates and protocols in place.

[neilmcc]

Thanks wainuitech. I'm actually using POP as I download emails onto my pc. If I change to IMAP will it upload all my emails from the past to the cloud? Got emails going back years. Periodically go through them on the pc to delete the ones we don't want.

[Wainuitech]

Yes you can move them,  ( and upload to IMAP), depending on how much you have it can take several hours to sync.

This is a good time to do clean outs, you know the times when we all will get around to it

1st and most important, go to your .pst file & make a backup copy.  This way If anything does go wrong you wont lose any mails.  Will also pay to backup your contacts.
Here is a  set of instructions,

Only Difference I do is go directly to the.pst file , normally in Documents/ Outlook Files  and copy/paste it to save

Number 4 I do differently ( but it does work)

https://help.one.com/hc/en-us/articles/3...OP-to-IMAP

Edited in:  To setup a New IMAP account some places go about it the long way ( manually) This article is how it works 99% of the time, Bascically Outlook does all the work /settings, only thing you need to know is your email address and password.

https://help.one.com/hc/en-us/articles/115005594485

IF you need to enter the settings manually they are listed in this link, they did change a while back to these 
https://support.microsoft.com/en-gb/offi...6c4ac95353

How I import the old .pst is shown in  the following article, near the bottom - "Restore Your mail Box"

https://www.hostpapa.com/knowledgebase/c...p-outlook/

[neilmcc]

Thanks wainui,I'll check that out. I assume that contacts are in the pst file, according to google.
I have Second Copy that backs up multiple folders every day ,including Outlook pst files.From the following folder.

In my C/Users/Name/AppData/Local/Microsoft/Outlook folder I have 2 folders..Accounts -with nothing in it...RoamCache with a few dat files in it,
1 archive.pst...50.3 MB
1 archive1.pst... 1.07 GB
and 1 Outlook.pst...3.23 GB

Not sure what the archive ones are for,any idea?
Thanks for your help and time.

[Wainuitech]

Thanks wainui,I'll check that out. I assume that contacts are in the pst file, according to google.
I have Second Copy that backs up multiple folders every day ,including Outlook pst files.From the following folder.

In my C/Users/Name/AppData/Local/Microsoft/Outlook folder I have 2 folders..Accounts -with nothing in it...RoamCache with a few dat files in it,
1 archive.pst...50.3 MB
1 archive1.pst... 1.07 GB
and 1 Outlook.pst...3.23 GB

Not sure what the archive ones are for,any idea?
Thanks for your help and time.

.pst is not normally in the AppDate/ ---- Location. The .ost is, which is IMAP.

Two ways to export it ( as a backup) as per the links, or open control Panel / Mail(Microsoft Outlook) Click on the Data Files Button, click your Account, then up top Open File Location. When open right click the .pst file - Copy Paste to someplace safe.

Contacts, usually don't come across with the .pst file.  Where as .ost (IMAP) will.

Open Outlook -- Top Left --- File - Open  & Export - Import/Export  (On the window that opens, from the list ) Export to a file - Comma Separated Values - Contacts - Select a location - Save.

You can open the .csv  file with Excel to check all the details have come across OK.

To put them Back, exactly the same from the new account, except select Import from another Program or File.

[king1]

also take a copy of the stream_autocomplete file in that Roamcache folder - it contains auto remembered email addresses in some outlook versions, and might get overwritten if you reload an email account

[neilmcc]

In Documents I've found the Outlook Contacts.CSV file which opens in Excel, so that's saved elsewhere now.
Thanks again, now to take it all in!