Examples of software where the new version is worse than the old?

iOS 26.

I can’t get over how ugly it looks. I guess it’s supposed to be transparent but often it just looks greyed out and edges of things look like they anti-aliased the images, took the residual, and sharpened the aliases just to make everything be surrounded by a distracting halo.

I appreciate the idea of having multiple windows on iPad (Win 8 had that how long ago?) but I was playing Arknights and the main UI trope in Arknights is you drag and drop your ‘operators’ from the edge onto the playing field and when I do that the whole window comes loose so I disabled that feature.

Every release of iTunes since SoundJamMP

Photoshop after somewhere between maybe 5 and CS2?

Office after maybe 2000?

CentOS after 8

Windows

Hardware: Lenovo ThinkStation <-- IBM PC AKA IBM 5150

Software: OmniGraffle 7 <-- OmniGraffle 6

Book: SICP (I like the 2nd edition best, now the latest based on Python is an aesthetic crime IMHO.)

For software, many programs reach the bloat status, of course there is the old joke about any system growing until it can send email (or having its own embedded LISP variant ;-).

Looking at the comments, might it be easier to list software with a track record of general improvement?

I remember one of the worst programs ever was from SAGE and it was called "Linha50". Originaly for MS-DOS, they converted it to Windows. The wait for a key on each field pushed the cpu to 100% because it was checking if there was any key being pressed.

Result, when "idle", the cpu was at 100%. Just imagine this.

Many users of Microsoft Word 5.1 for Macintosh hated Microsoft Word 6; they felt the latter was not Mac-like. I was a kid during this time and the only Mac word processor I used in the classic era was the one included with ClarisWorks, so I don’t have any opinions about Word 5.1 vs 6.

I feel Mac OS X peaked with Snow Leopard, though it wasn’t until Catalina when I started refusing to upgrade my personal Macs, which remained at Mojave until I retired them from daily driving.

I also remember SimCity (the successor to SimCity 4) and SimCity Societies not being well-received. Sadly the SimCity franchise is dead; I enjoyed SimCity 2000 and 4 (I never played 3000).

The fourth generation of Pokémon games, in my opinion, was the high water mark of the franchise’s main series games, peaking at Heart Gold/Soul Silver.

On the Mac, Final Cut Pro 7 to X was infamous.

And Aperture 3.6 to anything recommended to replace it.

Guitar Pro went downhill after version 5.

Winamp 2.9 was peak. They tried v3 and v5, but neither was loved like v2.