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I can have both the Skype for Business app and the normal Skype app open, take a screen shot, and paste into the normal Skype, but can't paste into Skype For Business. So it is not an issue on the Mac.
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Skype and Skype for Business are completely separate products, with separate functions. Albeit core functions seem to be similar and they are unfortunately named similarly but that is it.
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Scott, I believe I addresses your initial question...do you have any other questions?
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I contacted support, This was the reply, I have not had a Chance to call the number...<br />
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Resolving your concern is utmost priority and upon isolating your issue it requires special handling and I need to bridge you over to our Commercial Support Department to properly address this issue and have them resolve this for you since I'm only from Office technical support. For your reference, here is your case number 1413088767. Please be informed that I would be closing this off and Commercial Support Department will be creating a new one with your current issue. They will also be giving you a different case number.<br />
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You may reach them via: 1-800-936-4900. They are available Mondays to Fridays.
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FYI: Office365 is 24/7 and they typically respond in 15m.
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I'm using Skype For Business 16.13.184 on Mac OS 10.13.2<br />
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We are testing out Skype for Business with our Office 365 Business Premium license and the first thing I noticed is I cannot paste an Image from the clipboard into the chat. I can Attach an Image, but thats more work if I'm sending screen shots. &nbsp; Seems to work on Windows.
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I'm using Skype For Business 16.13.184 on Mac OS 10.13.2

We are testing out Skype for Business with our Office 365 Business Premium license and the first thing I noticed is I cannot paste an Image from the clipboard into the chat. I can Attach an Image, but thats more work if I'm sending screen shots.   Seems to work on Windows.

Paste an Image from clipboard in Skype For Business on OSX ?

Instant messaging (IM) is a type of online chat that offers real-time text transmission over the Internet. A LAN messenger operates in a similar way over a local area network. More advanced instant messaging can add file transfer, clickable hyperlinks, Voice over IP, or video chat. Non-IM types of chat include multicast transmission, usually referred to as "chat rooms". Depending on the IM protocol, the technical architecture can be peer-to-peer (direct point-to-point transmission) or client-server (a central server retransmits messages from the sender to the communication device).

Chat / IM

Microsoft Office is an integrated suite of applications that includes Outlook, Word, Excel, Access, PowerPoint, Visio and InfoPath, along with a number of tools to assist in making the individual components work together. Coding within and between the projects is done in Visual Basic for Applications, known as VBA.

Microsoft Office

All of Apple's hardware is produced solely by Apple Inc., who determines internal systems, designs, and prices. Apple buys certain components wholesale from third-party manufacturers. The current Mac product family uses Intel x86-64 processors. All Mac models ship with at least 1 GB RAM as standard. Current Mac computers use ATI Radeon or nVidia GeForce graphics cards and include a dual-function DVD and CD burner, called the SuperDrive. Current Apple hardware includes the iPad, iPhone, iMac, Mac Pro, Macbook, iPod and Apple TV. Discontinued hardware includes the Apple I, Apple II, and the Apple III, the Lisa, the Newton, the Quadra, Performa, Centris, Macintosh II and LC series, the Power Macintosh, iBooks and the MacBook.

Apple Hardware

Office 365 is a group of software plus services subscriptions that provides productivity software and related services to its subscribers. Office 365 allows the use of Microsoft Office apps on Windows and OS X, provides storage space on Microsoft's cloud storage service OneDrive, and grants 60 Skype minutes per month. Office 365 includes e-mail and social networking services through hosted versions of Exchange Server, Skype for Business Server, SharePoint and Office Online, integration with Yammer, as well as access to the Office software. All of Office 365's components can be managed and configured through an online portal; users can be added manually, imported from a CSV file, or Office 365 can be set up for single sign-on with a local Active Directory using Active Directory Federation Services.

Microsoft 365

Mac OS X is the desktop operating system from Apple Inc., found on Macintosh computers. OS X consists of a Mach/BSD-based kernel, operating system interfaces primarily based on FreeBSD and additional frameworks (written in C, C++ and Objective-C providing user interface and application-level services.

Mac OS X

Skype is for doing things together, whenever you’re apart. Skype’s text, voice and video make it simple to share experiences with the people that matter to you, wherever they are.

With Skype, you can share a story, celebrate a birthday, learn a language, hold a meeting, work with colleagues – just about anything you need to do together every day. You can use Skype on whatever works best for you - on your phone or computer or a TV with Skype on it. It is free to start using Skype - to speak, see and instant message other people on Skype for example.

Skype

Office Productivity refers both to the act of being productive and efficient in an office or professional environment, as well as the software applications used to "produce" information. This includes the development of professional skills, creating work processes, and almost any program used to create or modify a document, image, audio or video clip. However, business application suites such as Microsoft Office, which include word processing, spreadsheet and presentation programs, are typically called productivity software, as contrasted with a "utility program," such as a file manager, which is used to organize files and folders on the computer. Many office- and business-oriented groups of programs are organized into suites.