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So all of your internal clients that connect to sharepoint are able to open PDF without issue correct?<br />
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What version of IE our your clients using? Any Windows updates &nbsp;or Adobe updates installed recently?
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Is the sharepoint location trusted? &nbsp;It's usually the document &nbsp;type or Trust Center causing this.<br />
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- gurutc
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My be I am missing something here but I assumed that your PDF were working prior without the Adobe PDF handler?<br />
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&nbsp;If so what changed?
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Issue was resolved by Microsoft support.
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We have a SharePoint 2010 environment that we make available to via HTTPS. &nbsp;Our default options for document libraries are to open docs in a browser, but recently our PDF’s have been causing an issue. &nbsp;<br />
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When directly clicking on the pdf when you are not on the corporate network, you get the error “There was an error opening this document. &nbsp;The filename, directory name, or volume label syntax is incorrect.” &nbsp;This does not occur when on the network. &nbsp;<br />
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Furthermore, we discovered a workaround that when you use the dropdown for the document and select View Properties and then click on the document link from that dialogue box the file will open without error.<br />
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Has anyone experienced this?
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We have a SharePoint 2010 environment that we make available to via HTTPS.  Our default options for document libraries are to open docs in a browser, but recently our PDF’s have been causing an issue.  

When directly clicking on the pdf when you are not on the corporate network, you get the error “There was an error opening this document.  The filename, directory name, or volume label syntax is incorrect.”  This does not occur when on the network.  

Furthermore, we discovered a workaround that when you use the dropdown for the document and select View Properties and then click on the document link from that dialogue box the file will open without error.

Has anyone experienced this?

Error Opening PDF's in SharePoint 2010 when connected over https

Microsoft Sharepoint is a software platform and family of software products used for collaboration and web publishing combined. These capabilities include developing web sites, portals, intranets, content management systems, search engines, wikis, blogs, and other tools for business intelligence and collaboration. SharePoint has a Microsoft Office-like interface, and it is closely integrated with the Office suite.

Microsoft SharePoint

The Windows operating systems have distinct methodologies for designing and implementing networks, and have specific systems to accomplish various networking processes, such as Exchange for email, Sharepoint for shared files and programs, and IIS for delivery of web pages. Microsoft also produces server technologies for networked database use, security and virtualization.

Windows Networking

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.

Windows Server 2008

Networking is the process of connecting computing devices, peripherals and terminals together through a system that uses wiring, cabling or radio waves that enable their users to communicate, share information and interact over distances. Often associated are issues regarding operating systems, hardware and equipment, cloud and virtual networking, protocols, architecture, storage and management.

Networking

HTTPS is a protocol for secure communication over a computer network which is widely used on the Internet. HTTPS consists of communication over Hypertext Transfer Protocol (HTTP) within a connection encrypted by Transport Layer Security (TLS) or its predecessor, Secure Sockets Layer (SSL). The main motivation for HTTPS is authentication of the visited website and to protect the privacy and integrity of the exchanged data. HTTPS is widely used for protecting page authenticity on all types of websites, securing accounts and keeping user communications, identity and web browsing private.