Some time ago, I discussed the intended uses of the icons in progman.exe and moricons.dll and we even looked at those icons (progman.exe, moricons.dll).
But what about pifmgr.dll?
The pifmgr.dll file was added in Windows 95. 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.
Whereas the icons in moricons.dll were created with specific programs in mind (list) and the icons in progman.exe were created for general categories of applications, the story behind the icons in pifmgr.dll is much less complicated.
The icons in pifmgr.dll were created just for fun. 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 own homemade shortcut files.
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MS-DOS logo |
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Umbrella |
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Play block |
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Newspaper |
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Apple with bite |
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Cloud with lightning |
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Tuba |
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Beach ball |
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Light bulb |
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Architectural column |
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Money |
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Desktop computer |
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Keyboard |
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Filing cabinet |
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Desk calendar |
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Clipped documents |
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Crayon with document |
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Pencil |
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Pencil with document |
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Dice |
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Window with clouds |
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Eye chart with magnifying class |
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Dominos |
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Hand holding playing cards |
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Soccer ball |
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Purse |
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Decorated tree Wizard’s hat with wand |
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Race car with checkered flag |
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Cruise ship |
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Biplane |
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Inflatable raft |
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Traffic light |
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Rabbit |
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Satellite dish |
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Crossed swords |
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Sword and shield |
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Flail weapon |
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Dynamite and plunger |
I don’t know if it was intentional, but I find it interesting that clouds were the theme image for Windows 95, and we have a window with clouds. At the same time we have an apple with a bite, but the bite is on the left hand side, as opposed to the right hand side in the logo of Apple Computer.
Coincidence? Tip of the hat? Subtle jab? You decide.
The “window with clouds” icon reminds me, thematically, of the icon used in the about window of really early builds of Windows 3.1 (except that one is curved at the top, and the sky color is a lighter tone).
I run a query on an AI model:
Fun puzzle. Here’s what jumps out if you “read” the strip from top to bottom and connect them like a story rather than as random clip-art:
It opens with MS-DOS → a nod to Microsoft’s origins.
A quick “umbrella / A-block / newspaper / apple / lightning” run looks like scene-setting (brand under one umbrella, basic building blocks, press, the Apple rival, a stormy inflection point).
Then a cluster of work/Office motifs: light-bulb (ideas), column (pillars), money, desktop / keyboard / filing cabinet / calendar / documents / pencils → files, editing, clipboard/“Clippy” vibes.
Dice → Window...
You may want to have your AI checked for paranoia or schizophrenia.
Nothing to check for. The AI must find patterns so it will amplify noise if there are none.
However, given the icons in random order; the human placing them will want to place them into logical groups, so finding logical groups in a manually ordered collection of icons is expected.
Yes — that cluster is a hidden “Office stack” roll call.
Light bulb → PowerPoint (ideas/presentations)
Architectural column → Excel (columns/spreadsheets)
Money → Excel again (budgeting/finance)
Filing cabinet → Access (database/records)
Desk calendar → Outlook (calendar/email/PIM)
Clipped documents → Clipboard/Clippy (Office clipboard & the assistant vibe)
Crayon with document → Publisher (layout/desktop publishing)
Pencil / Pencil with document → Word (edit/write documents)
Desktop computer + Keyboard → the Windows workbench tying it all together.
Read as a workflow: ideate → model/budget → store data → schedule → draft → design → edit/polish — i.e., Microsoft Office, not just generic “work” icons.
I will take these over the amorphous, colorless blobs that are modern icons any day!
And I still use them to this day!
Pretty sure that Apple icon is a nod to the company of the same name. If you flip it so that the bite is on the right side, the apple’s leaf also points the correct way.
When I was a kid, I was sure that “money” is a circuit board (green bank notes were not common in my country) and “rabbit” is a spaceship
I loved to set icons for DOS programs. At first I tried to find appropriate icon, with meaning, but I quickly switched just to set fun or bright one 😁
Sexy. They don’t draw this pixel art anymore.
Wow, memories. Cruise ship for Civ, swords for Warcraft. Played on a massive 2-foot-tall tower with incredibly heavy monitor.