"Microsoft filled pifmgr.dll with a selection of icons that a user might find handy to represent an MS-DOS application on the Windows desktop. "The pifmgr.dll file was added in Windows 95," explained Chen. "Its job was, as the name might suggest, to manage PIF files, which are Program Information Files that describe how to set up a virtual MS-DOS session for running a specific application.""
""The icons in pifmgr.dll were created just for fun," he said. "They were not created with any particular programs in mind, with one obvious exception. They were just a fun mix of icons for people to use for their homemade shortcut files.""
"Or perhaps the Microsoft team that came up with them all those decades ago had glimpsed the future and wanted to use pifmgr.dll to warn future generations. There is, for example, a window through which clouds can be seen - a reference to Azure for sure. Then there is an image of a cloud with lightning - surely a warning about this week's catastrophic AWS outage. There's also a play block on which the letters A and I are seen (OK, it's probably A and the number 1, but let's not quibble about details). And finally, there's an apple with a bite taken out of the left side instead of the right side of Apple's famous logo. Chen speculated: "Coincidence? Tip of the hat? Subtle jab? Yo"
pifmgr.dll persists in contemporary Windows installations and houses a collection of small, blocky icons from the 16×16, 16‑color era. The file was added in Windows 95 to manage PIF (Program Information Files) that configure virtual MS‑DOS sessions for specific applications. The icons were intended to represent MS‑DOS shortcuts on the desktop and were largely playful, not tied to particular programs. The collection echoes earlier icon libraries such as moricons.dll and progman.exe, and several images invite retrospective interpretation, including cloud motifs, a play block labeled A/I, and an atypically bitten apple.
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