Display A Caution In Outlook Desktop App If Many Recipients On Send - outlook

How would I display a caution to the user in Microsoft Outlook 365 Desktop App when, on send email, if count of recipients is greater than, say 10, an 'Are you sure? (n/Y)' dialogue is displayed to user.
If Y, email is sent.
If N, dialogue closes.
I'm trying to solve the GDPR / data privacy problem where hundreds of recipients are added to the Cc line instead of Bcc by mistake.
The 'Large number of recipients or contact group' MailTips feature is helpful but not working for us.
David.

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On-send add-in not loading after Outlook error

I am developing an Outlook 'on-send' add-in which loads a dialog box if the email is addressed to multiple recipients after the send button is pressed. In the dialog, the user confirms the intended recipients from a list and then presses send. The add-in then allows the send event to happen.
A problem arises if the emails are not formatted correctly; Outlook throws a ‘does not recognise email’ error after trying to send the email. The problem is that when I try to send the email again after the error, the add-in does not load. The add-in should load every time the user tries to send an email to multiple recipients.
Please see a video of this behaviour here: https://youtu.be/U1VFuy1qbHM
As you can see from the video, the email goes to my Outbox fine after the first send. However, Outlook throws an errors when I edit the email in my Outbox and try to send it again (presumably because I was using a made up email to test with). As you can see, if I then update the emails and click send, the email sends without the add-in loading again. The intended functionality of the add-in is that another dialog box should be displayed in this case.
This behaviour also occurs when you reply to an email where the recipient has their email address formatted differently. For example, 'Name Surname (name.surname#domain.com)' instead of 'Name Surname <name.surname#domain.com>'. Outlook does not seem to like this format and throws a similar error after trying to send the email. After updating the email format and clicking send, the add-in does not load again.
The error occurs in Win32.
I do not think the problem is with the Javascript. I think the add-in does not even load when I try to resend the email. Maybe the add-in is somehow holding onto the ‘True’ value of the on-send event from the previous dialog box? I have tried editing the different ‘ReadorEdit’ values in the Manifest file to try and ensure the add-in loads for all cases but it has not helped.
What can I do to ensure the add-in loads after these errors?
Thank you for your help- it is very much appreciated.

Outlook New Message - Text Area Below Toolbar

I am creating an addin for Outlook.
I want to check some text on sending, but im not sure how to reference it
The text is in the image below and says “Attachment will be sent using...”
If the text equals the text displayed, i want to do something.
Thanks for any advice.
The Outlook object model doesn't provide anything for reading mail tips. But you may consider using EWS for getting mail tips. See Using MailTips in EWS to get the OOF (Out of Office) Status of users with C# and Powershell for the sample code.
FYI MailTips are informative messages displayed to users in the infobar in Outlook Web App and Outlook 2010/2013/2016 when a user does any of the following while composing an e-mail message:
Add a recipient
Add an attachment
Reply or Reply all
Open a message from the Drafts folder that's already addressed to recipients
To configure MailTips for mailboxes, external contacts, and distribution groups, in the Exchange Control Panel, select the mailbox, external contact, or distribution group, click Details, and then in the MailTip section, create the MailTip.
To configure MailTips for mail users and dynamic distribution groups, in Windows PowerShell, use the MailTip parameter on the Set-MailUser and Set-DynamicDistributionGroup cmdlets.
Regardless of whether you use the Exchange Control Panel or Windows PowerShell, two things always happen when you add a MailTip to a recipient:
HTML tags are automatically added to the text. For example, if you enter the following text: This mailbox is not monitored. The MailTip automatically becomes the following: <html><body>This mailbox is not monitored.</body></html>
The text is automatically added to the MailTipTranslations property as the default value. If you modify the MailTip text, the default value is automatically updated in the MailTipTranslations property.
Read more about that in the Configure MailTips article.

Delay emails sent and received through IMAP

I want to put emails the user receives in a sort of "review status" in my app and let users choose manually if they want them to be let through.
For this I need to filter network traffic to withhold emails receivef with the IMAP protocol from Outlook and send them some time afterward. And to the same for emails being sent.
Would this be possible to do on Outlook on Windows 7/8? Or would I be unable to make Outlook receive the mailing after I filter it out?
The Outlook object model doesn't provide anything for foltering emails.
Instead, you may consider handling the new email programmatically in the code handling the NewMailEx event which is fired when a new item is received in the Inbox. For example, you may develop a VBA macro for doing any customizations in Outlook programmatically. See Getting Started with VBA in Outlook 2010 for more information.

End Event on Room Resource calendar

The problem that I face: I currently use a product that displays calendar items on an iPad outside of conference rooms. I have all the room resources set up and everything works brilliantly except if I try to end the event early from this display.
The reason it doesn't end: When User A schedules a meeting and adds the room Conference Room as a resource, and Conference Room accepts, the meeting is still owned by the organizer, or in this case User A. Because of this, the room itself can not edit times on an event, only the organizer can.
The question: Is there any way, to have the Room auto accept the meeting, and also be able to edit the event?
Please note, I have tried this with Exchange 2007, Exchange 2010, Exchange 2013, and Office 365. The servers have been both on-premises and hosted.
No the only valid editor of a Meeting is the organizer for the reason that each copy of the meeting stored in the Attendees mailboxes is a separate item in the Exchange Mailstore. Eg Even if the Organizer modifies the appointment and doesn't send out Meeting updates the changes they make won't show on the attendees (or Room Mailbox) calendar until the updates are sent and accepted. This is fundamental to the way in which Appointments work if you need to change a meeting for some reason you may want to look at impersonating the Owner of the Appointment in EWS. The one thing the Room mailbox (or any attendee) could do is propose a new meeting time which would be a separate message that would sent back to the Organizer who then once they accepted would send out a normal Meeting update to all attendees.
Cheers
Glen

Outlook calendar disappear from inbox after accept the request

Outlook 2010 and 2010+ versions seem to remove meeting request emails from your inbox once you accept or decline the invite.
How do I prevent these from being removed and keep them in my inbox?
Usually the meeting invite also contains useful information or things that need to be followed up later.
In Outlook, this is found under the File tab. Click Options, then Mail, and scroll down to the Send messages section. Uncheck the box next to Delete meeting requests and notifications from Inbox after responding
The provided "ounce of prevention" instructions are spot on! However, when faced with the immediate dilemma of needing the email... one goes to the Deleted Items folder to find the email, BUT (because the invitation email may be prevented from opening by Outlook) one must click Reply to then be able to once again read (and hyperlink-click) the original email entries.
I just did this, but with the Outlook web (Office 365) it's a little different now. To stop calendar invites being deleted do the following:
Go to the settings wheel > View all Outlook settings > Calendar > Events and invitations > uncheck the box 'delete invitations and responses that have been updated'

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