Trouble with password protected PDF emailed to client with Windows 10 and Office 2016 (Outlook) needing 64 bit encryption?

[fallbrookian]

Since upgrading to Windows 10, I can no longer send a password protected pdf copy of tax return. Error says Outlook is not my default email program. It is and is set up properly as verified by Tech today for over an hour). I can also email from home base through outlook so it does recognize it. I Got a long song and dance from tech support about it missing a windows object. I use Outlook 2016 from Office Suite 2016. It worked perfect before Windows 10 update. Now, if you use Outlook 2016 with Windows 10 you are required to X the box "Use 64 bit email client (Outlook 2016 only)" in tools, options. I believe this is the problem. I am asking ProSeries to help figure this out not just pass it off with a data structure blurb that makes no sense. Please Intuit - care about us tax pros who use ProSeries Pro not just the Turbo Tax millions. 

[Accountant-Man]

I have never used a PS password protected PDF file because it goes through Outlook, and I don't use Outlook for email.

Instead, you can just print it to a password protected PDF and later find it and attach it to an email or use a portal.

[fallbrookian]

Hi – Thank you. Certainly I am well aware that I can simple attach a PDF to an email and send it without password protection. However, this password protected email of the return has been available on Pro Series for years. Many of my clients want their sensitive date password protected in an email. I want to use what is in the program available to all – it’s a valuable time savings tool rather than uploading to a portal and having them download it etc….and it’s included in the price of ProSeries. We should all be more careful with emailing sensitive data. BTW – it’s not necessary to use Outlook to use the ProSeries password protected tax return email option.

[Accountant-Man]

I said, "Instead, you can just print it to a password protected PDF" and then attach it to an email. You don't have to send an unprotected one.

[fallbrookian]

Agreed that is a work around. Then I have to send a separate email to give the client the password. it works, it;s just a few more steps and I prefer to use the benefit the program offers. There is a way to fix this problem with Windows 10 and Outlook 16 - they should.

[Just-Lisa-Now-]

I just saw an option in 2019 when I installed it that had a checkbox for 64bit email, but now that Im back digging through it looking for it, I cant find it again!

[Just-Lisa-Now-]

Ahhh there it is....Tools >Options > General at the very bottom of the window is a checkbox for 64bit Email client

[fallbrookian]

Thank you, I have that checked and wonder if that is the problem. The agent on the phone that was trying to help - kept saying we need 32 bit and looking to see if all programs were 32 bit.

[Just-Lisa-Now-]

Sorry, Ive never emailed a pdf directly from the program, Ive seen lots of people struggle with it, figured I didnt need any extra hassles, I dont even use the pw protect pdf option in the program, I use Bullzip to pw protect, then send in a regular email.  I know, old school, extra steps, but never had an issue with it.

[dbelling]

I do no see the button...send pdf at all now that I have windows 10....very frustrating..and i dont want the workaround either...anyone get a solution as yet

[Ted2]

You are a genius!

[musiccitycpa]

I think the solution is to switch to another tax software program next year.  Very frustrated that this very important and useful feature is not available, or if available, not working.

[JeffCPA]

Yes, I am having trouble with the password protect email approach as well.  I use Windows 10.  I just got a new laptop with Windows 10.  In prior years this worked fine when I was using an earlier version of windows. 

Now when I use the email feature within proseries to email to clients, it goes through the process of sending the email, and at the end I get a message saying "error. email could not be sent."

In fact, the email to the client has been sent (clients have advised me of this) and I am getting my preparer's copy of the same email in my outlook in box. 

However, the actual password protected pdf that is supposed to be generated and saved to the "emailed" folder is not being generated.   

So, in other words things are kind of working.   It is a hassle.   I was on the phone with a proseries tech on this issue, after waiting an hour, and his fix was to preview the password protected pdf and then save it separately as a pdf, and then email it separately to the client.   A hassle and time consuming and of course, means they don't care about fixing their software. 

[dsocpa]

The "send client tax return option is not showing up at all on the Print screen?  I did check the 64 bit email box.  Did ProSeries eliminate the send PDF option?

[ehunter]

If a valid and secure file sharing platform, such as Citrix File Share is implemented, the files can be printed to the platform and clients can receive them.  Upload and download are encrypted and this approach eliminates the traditional Outlook hassles, plus you can receive verification when a client receives their data and notification if they send something back to you once you properly set up the permissions.

[dsocpa]

I use LeapFile secure send to email.  It's not a good idea to email tax information through traditional email (outlook, gmail, etc.).  I liked ProSeries send because it wasn't just a protected PDF.  Password protected PDF's are not secure.

[ehunter]

Agreed.  Office 365 E3 and E5 have encrypted connectivity options for MS Exchange.  Additionally Adobe Acrobat will encrypt, as will a paid WinZip application (if you want to take an extra step).  Citrix Share File also provides encrypted connectivity to and from for both the preparer and the client.

[C4U]

After a quick overview - I looked at Citrix mentioned in another comment and LeapFile you mentioned.  So you are happy with LeapFile?  It seems much more cost effective than other options I've looked at.  For an individual I cannot bear much overhead so trying to be effective, secure yet cost conscious.  I appreciate your experience and feedback.