Can`t add attachment to mail

[Respigi]

I`m trying to add a small photo as an attachment to an email. This is what I`m doing.
           Scan photo in printer scanner.  Import to My pictures in PC. Win 7.
           Open new email ( I`m using Hotmail) and drag photo from Pictures to mail area.
           Send email to myself with comments.
   Sometimes mail gets thru` with message but no photo, but most times gets a Microsoft message saying Error occurred.
   All mail gets thru` always with text only.

[Respigi]

or further to this I can Rt. click on image and open with Windows photo viewer.
Image shows in email area and I can post to myself.
 Same result as above.  Mail error 3209 occurs

[patio]

Are you naming the photo and saving it proper ? ?

Also which email client / ?

[Geek-9pm]

Questions.
Has it worked before?
What email tool do you use?
What is the type and size of the Photo?
Here is a link for email error codes:
https://support.microsoft.com/en-us/help/942495/windows-mail-and-windows-live-mail-error-codes
But 3209 is not listed. Here is a reference to 3209:

The error Windows Live Mail Error ID: 0x8DE00006 pertains to account is temporarily deactivated and what you received is called HIP. It is part of the Human Interactive Proof (HIP) validation process. We have implemented it to verify valid users and to help stop both incoming and outgoing unsolicited messages (spam).

If you're not seeing the picture with characters and numbers when accessing account using Windows Live Mail or any email client, I suggest you access your account on the web based mail and check if the HIP will appear there. Once it appears, fill out the information there and submit. If issue will persist, clear your browser's cache and cookies or use a different browser or computer in verifying your account.

https://answers.microsoft.com/en-us/windowslive/forum/livemail-sync/server-error-3209-windows-live-mail-error-id/30204e5a-e552-4462-9256-a3e07bc19e27
Does this seem relevant?

[Respigi]

Thank you both for replying.
     Mail is Hotmail and am not using any tools. Works for all mail text and photos in but not with my photos out.`
     Haven`t sent photo attachments before so can`t comment on past performance. Photo size is 100mm by 78 mm. black and white.
     When I click on Properties of photo in Pictures shows size as 36MB but when I open with something it shows size as 230Kb.
     It is this 230kb that I attach to a new email. The name is what it shows as in the Pictures file.
     Sending this is now giving an error message 0x8DE00005.
   

[Geek-9pm]

Respigi,
Did you already try this?
Go to https://account.live.com/ManageSSL Login with your Windows Live ID (Hotmail ID) and click the following radio button: Don’t use HTTPS automatically. Click the Save button. This will turn off the HTTPS security feature.
https://answers.microsoft.com/en-us/windows/forum/windows_xp-networking/windows-live-mail-error-id-0x8de00005/84aa40f5-37ab-4a23-afd9-c1212eabbac5
Edit: Bad link. try https://account.live.com and see if it is possible to disable the https  feature.