OpenOffice Writer email merge using Outlook.com (free) email

[BoomerApache]

I appreciate any help to configure OpenOffice Writer (version 4.1.6, Build 9790) to eMail merge with my outlook.com (the free version, also called "Microsoft Mail"). I am running this on Windows 10 operating system.

Let me know if additional information is needed to help solve this issue, and any solutions for a fix.

What I have tried so far, and the associated error messages I have received include:

Went to tools, options, openoffice writer, mail merge e-mail section and entered the following:

Your name - <my name>
E-Mail Address - <my email address> ("name@,outlook.com"
Outgoing server (SMTP) Settings
Server name - outlook.office365.com
Port - 587
Under "server Authentication" button
Left unchecked the box for selection - "The outgoing mail server (SMTP) requires authentication"

Test Setting (using "Test Settings..." button) exercise resulted in all Green "Establish network connection" = Successful; "Find outgoing mail server" = Successful

Completed a test email merge using the Writer email merge steps (using a Calc spreadsheet to hold email <address> and <firstname>, created a Writer document that includes the <address> and firstname> fields) and some static verbiage. Note: In the Calc spreadsheet the 1st and 3rd email address is set as html link and the 2nd email address set as text.

Tools, Mailmerge Wizard,
1. Select starting document = "start from existing document" (selected writer document with <address> and <firstname> fields and static verbiage
2. Select document type = "E-mail message"
3. Select address list = selected "Select Address List..." button, selected Calc spreadsheet that includes <address> and <firstname> data for 3 test email address
4. Create Salutation = left box unchecked-no salutation
5. Adjust layout (selection was greyed out-possibly due to this being an email?)
6. Edit document = no actions taken
7. Personalize Document = no actions taken
8. Save, print or send = "Send merged document as E-Mail", in E-Mail settings entered "address" in "To" field and "test" in "Email settings" "Subject" field
Selected "Send documents" button

Sending E-mail messages Window opens and displays the following:
Connection Status - The connection to the outgoing mail server had been established
Transfer status - 1 e-mails sent - Sending Paused
Task window shows RED X and Sending to: <test email address #1", and "Status" Sending failed (invalid address)

"Emails could not be sent" window opens with the message "The following error occurred:" and the following "Detailed information":
(for first email merge email attempted)
<class 'smtplib.SMTPHeloError'>: (501, '5.5.4 Invalid domain name [MN2PR10CA0007.namprd10.prod.outlook.com]'), traceback follows
C:\Program Files (x86)\OpenOffice 4\program\python-core-2.7.6\lib\smtplib.py:538 in function ehlo_or_helo_if_needed() [raise SMTPHeloError(code, resp)]
C:\Program Files (x86)\OpenOffice 4\program\python-core-2.7.6\lib\smtplib.py:711 in function sendmail() [self.ehlo_or_helo_if_needed()]
C:\Program Files (x86)\OpenOffice 4\program\mailmerge.py:267 in function sendMailMessage() [self.server.sendmail(sendermail, truerecipients, msg.as_string())]

attempt to send email #2 resulted in the following message

(for second email merge email attempted)
<class 'smtplib.SMTPSenderRefused'>: (503, '5.5.2 Send hello first [MN2PR10CA0007.namprd10.prod.outlook.com]', u'myname@outlook.com'), traceback follows
C:\Program Files (x86)\OpenOffice 4\program\python-core-2.7.6\lib\smtplib.py:724 in function sendmail() [raise SMTPSenderRefused(code, resp, from_addr)]
C:\Program Files (x86)\OpenOffice 4\program\mailmerge.py:267 in function sendMailMessage() [self.server.sendmail(sendermail, truerecipients, msg.as_string())]

attempt to send email #3 resulted in the following message

(for third email merge email attempted)
<class 'smtplib.SMTPSenderRefused'>: (503, '5.5.2 Send hello first [MN2PR10CA0007.namprd10.prod.outlook.com]', u',myname@outlook.com'), traceback follows
C:\Program Files (x86)\OpenOffice 4\program\python-core-2.7.6\lib\smtplib.py:724 in function sendmail() [raise SMTPSenderRefused(code, resp, from_addr)]
C:\Program Files (x86)\OpenOffice 4\program\mailmerge.py:267 in function sendMailMessage() [self.server.sendmail(sendermail, truerecipients, msg.as_string())]

Again any help is appreciated.

[RusselB]

Welcome to the Forums.
While I did read your detailed (appreciated) message, I think that the main problem you might be running into is the fact that OpenOffice cannot be configured to work with an online mail service.
While I'm not positive, I believe Microsoft Mail is an online mail service. You can either confirm this, deny this, or provide some additional information which, in turn, will confirm or deny this.
If you don't know for sure, then answer one of these questions: Do I have to go an online website to access my e-mail? or Do I have an e-mail program installed?
If you can answer the first one with Yes and/or the second one with No, then you have an online e-mail account, and OpenOffice cannot be configured to work with it.
You would need to install a 3rd party e-mail program. Thunderbird is, quite often, recommended for this.
If you answer the first one with No and the second one with Yes, then OpenOffice should be able to be configured to work with your e-mail server.

[BoomerApache]

I believe online, but...
Outlook.com is a web based email service. There is the "Windows Mail" app (I use Windows Mail on Windows 10 OS to connect to my outlook.com email) that connects to Outlook.com and other online email services (i.e.: gmail, yahoo, etc,). There is also the ability to use a browser to access outlook email.

Are you suggesting Open Office eMail merge only works with 'in house' email systems like Exchange?

[keme]

...
Are you suggesting Open Office eMail merge only works with 'in house' email systems like Exchange?

I checked the outlook.com support pages, which give the information you said you entered, and a little more info:

• The service requires authentication which you said you unticked. Same credentials for incoming and outgoing connection.
• The support pages for the mail service says it uses TLS, so tick "Use secure connection".
• The server may check for a valid sender email address, so remove the comma after @.

[Hagar Delest]

Are you suggesting Open Office eMail merge only works with 'in house' email systems like Exchange?

No,it works with email clients installed on the machine. That is an application, not a web service.