Testing Email server Exchange Server 2010 manually - sending a email with attachment

I have a process that will create a PDF attachment and then send the attachment via automated program.  Recently the program has a problem finding the attachment.

How can i test sending a emali with a attachment?

I like to test this process by creating a test that will first test our email server.
I have tried the telnet process and i am not getting a postive when I run the EHLO command.

(Start communication by typing the following command:
EHLO test.com
If the command is successful, you receive the following response:
250 OK)

This does not happen, all I get is:

220 Bmail.corp.biotone.com Microsoft ESMTP MAIL Service ready at Thu, 9 Jul 2015
 10:18:40 -0700

EHLO BIOTONE.COM
250-Bmail.corp.biotone.com Hello [64.73.243.232]
250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM LOGIN
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250-XRDST
250 XSHADOW

SHOULD IT RETURN 250 OK?
Scott JohnstonIT Manager Asked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

x
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Will SzymkowskiSenior Solution ArchitectCommented:
You can use the Send-MailMessage to send test emails with or without attachments.

Will.
Scott JohnstonIT Manager Author Commented:
Will, sending attachment via my Outlook clients works fine.  So I not sure using Powershell would test the process the same as it is being run currently.
I like to test my proecess run from a network resouce, not directly on the mail server?

Any ideas?
Will SzymkowskiSenior Solution ArchitectCommented:
Well that really depends on if the device supports sending email. If it does all you need to do is create a receive connector for anonymous and reference the IP of the network device. This will allow you to send email anonymously from that IP.

Will.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
Scott JohnstonIT Manager Author Commented:
I think we are on differnt pages.
My process that i have currently will create a PDF file, then the PDF file is attached to a email using a customer program(proprietory-I'm trying to get the vendor to support their development, but they want me to upgrade...Instead of supporting a older version)

So I wanted to create a homegrown solution to test the same process.

Invoice is genereated, then the invoice is converted to a PDF
Scott JohnstonIT Manager Author Commented:
thank you
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Exchange

From novice to tech pro — start learning today.