I've written several times here about all the mistakes that Sun made during the 00s that doomed it. Among the many mistakes it made are:

- Cancelling -if briefly- Solaris on x86 in 2002. This killed Solaris in the minds of many who didn't want to be locked into Sun for SPARC.

- Failing to make a deal with Google in 2002. Apparently Sun insisted on knowing how many servers Google had, something that Google considered a high-value secret, so Sun failed to make a deal with Google, so Google ended up using Linux and contributing to Linux. This was a tremendous mind-share disaster -- it's hard to overestimate the damage done by this.

- Closing Sun PS (professional services). Bad bad move, possibly the worst of them.

- Not giving up on J2ME earlier -- it's not the sort of thing that could last forever, and Steve Jobs killed it with the iPhone. This was a case of vendor lock-in clouding Sun's decision making.

- Failure to recognize that Sun needed to become a systems company, not a CPU company.

- Failure to respond to Active Directory. This was yet another case of vendor lock-in clouding Sun's decision making: the Sun DS product team was milking their existing customers more than they wanted to go after more business with a sustainable strategy.

- UltraSPARC was more than a decade too late to make up for SPARC falling way behind x86_64. Sun needed to give up on SPARC, but again, vendor lock-in sounds sweet but turns out to be poison.

- Failure to make a deal with Apple for it to use ZFS in OS X.

- The MySQL purchase. WTF, this was horrible and stupid. The only interesting effect of this was to make Sun a target of acquisition for Oracle. But of course, it turns out that Oracle -a company built on building mind-share- had become too blinded by vendor lock-in just like Sun, so...

There were numerous other mistakes along the way. These are the most salient, for me anyway.

What's shocking is how long it took Sun to fail under those circumstances!

Also shocking is how much amazing stuff came out of Solaris engineering and the systems division!

> - UltraSPARC was more than a decade too late to make up for SPARC falling way behind x86_64. Sun needed to give up on SPARC, but again, vendor lock-in sounds sweet but turns out to be poison.

UltraSPARC came out in 1995, and Athlon 64 in 2003. I'm confused on how it could be late?

> - The MySQL purchase. WTF, this was horrible and stupid. The only interesting effect of this was to make Sun a target of acquisition for Oracle. [..]

I disagree with this assessment strongly. I believe Oracle wanted Java and only Java. All other Sun properties were collateral damage of the acquisition. It might be weird that Oracle now owns MySQL, but Oracle never cared about it. (Of course, both your and my assessment are mere opinions.)

> UltraSPARC came out in 1995, and Athlon 64 in 2003. I'm confused on how it could be late?

Ah, sorry, I was referring to the CMT architecture.

My brain: Country Music Television? Rather, it's Chip Multi-threading Technology.

https://en.wikipedia.org/wiki/SPARC_T_series

Oh geeze I went from an UltraSPARC III to a T1 and performance tanked.

Turns out my use case was not large numbers of parallel integer only threads.

> Failure to respond to Active Directory

Sun did really well in the academic workstation market, converting the old "VAX and a sea of terminals" into a "sea of Sun workstations".

X11, YP/NIS and NFS worked pretty well for a while, but then Microsoft came out with NT and AD, and Sun failed to respond. Like, ever. I think this was perhaps the worst software mistake Sun made.

I tried to sell XAD, the Active Directory workalike I wrote 2002-2006, to Sun. Would’ve integrated nicely with SunDS (a big part consisted of SLAPI plugins). Was in touch with Jonathan Swartz, but no dice. Sold it to Novell instead. Ironically ended up porting SLAPI to eDirectory to integrate it.

I didn't know you tried at Sun. Obviously I was a big XAD fan :-).

I pushed XAD internally. But I didn't have the pull needed.

Sun not acquiring XAD was a big mistake.

It's worse because huge chunk of Active Directory is essentially building on what MIT Athena did, which was heavily used with Sun as well - and all packaged into something that can be brought up operationally by SMB team with no previous experience

Building an AD-compatible service is not that easy, and it was not easy circa 2006, because there was a lot to reverse engineer. Sure, Sun had access to its own directory service (Sun DS), MIT Kerberos, BIND, OpenLDAP, NSS, and Samba, so it had a lot of the pieces, but there was a lot of work to be done putting everything together.

For sure. But Sun had great engineers, and it was a feature that I'd argue was visibly existential at the time.

Yes, Kerberos is a direct import, although extended quite a bit. AD is a lot more than Hesiod, but AFS is a lot more than SMB. Zephyr didn't make it over.

There was an opportunity to build out graphical management tools, but NIS+ kinda got in the way, and the politics of commercial Unix in general didn't help.

The nice thing with kerberos is that it v5 has extensibility effectively built in :)

I'd say the switch to DAP/LDAP was obvious better choice than Hesiod, and GPO essentially standardizes a lot of tooling that SIPB et al built for Athena as well

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> The MySQL purchase. WTF, this was horrible and stupid. The only interesting effect of this was to make Sun a target of acquisition for Oracle.

Strong disagree with this!

The MySQL purchase wasn't a lot of money and was a move towards becoming a systems company (like you suggested they need to be)

Oracle bought Sun for Java, not for MySQL.

My memory is that Oracle bought Sun for the Java lawsuit, not Java itself.

Oracle sued Google over Java - it wasn't some previously existing case.

Yes, it is Oracle so there's a great chance they were considering this when they bought it.

The disagreement had been going on for years (at least since Google launched android, perhaps before that), Google and Sun had been in “negotiations” that were publicly documented as going nowhere. All that had happened is Google implemented more “workarounds” to use less of Sun’s IP.

I actually remember media speculating that Sun didn’t want to take the next step and actually file a lawsuit, because they didn’t have enough resources to go up against Google in court.

Then Oracle bought Sun, and suddenly the unproductive negotiations transformed into a lawsuit.

And thanks to that lawsuit, we got to see Oracle lose (always nice!) and SCOTUS establish that using APIs constitutes fair use (awesome!)

At least they had the intelligence not to sue Google. I wonder how much money Oracle lost on that debacle. (The policy loss is big enough to them on its own! SCOTUS made the right call.)

IIRC the writing was on the wall by 2002. The x86 hardware was finally good enough that first there was a lurch to WinNT, then Linux once people realized NT wasn't as stable or developer friendly.

That's when I went to work for them. As far as forming my career went, it was a great move. And since it was Solaris engineering I went to, it was quite fun. But yeah, Sun was done -- it just didn't know it, and it spent almost a decade making mistake after mistake. I do think Sun could have been much more successful if senior management had made better decisions, in particular if they'd committed to x86_64 as the future.

Thanks for sharing. What do you think was the reason that the hardware part of Sun failed to keep up with competitors? Specifically why UltraSparc failed to match Pentium?

CPU design is expensive. Intel was ahead of the competition and wasn't fabbing, so Sun was a generation behind. That sort of thing.

Note that today things are quite different, and Apple can do what Sun wanted to do, but do it well. Market conditions are very different, and Apple, of course is the 800lb gorilla that Sun couldn't quite get to be. It's kinda funny: Apple and Sun weren't all that different, and Sun then and Apple now even more so. Apple just wasn't into servers, and Sun just wasn't into consumer hardware, but both wanted to vertically integrate hardware and software. Apple has a walled garden, Sun didn't. I do think these differences are relevant to why Sun failed, but the leadership differences count for a lot too: no one would compare Steve Jobs to Jonathan Schwartz, nor even to Scott McNealy -- it's just night and day. Now the differences in what Sun and Apple sought to do also evince differences in leadership.

Thanks for sharing. I know nothing about CPUs themselves so was curious. I always thought that Sun was into the more premium stuffs, but then I realized that Intel actually caught up with commodity chips. The other workstation/server companies seemed to fall into the same path unfortunately so I guess Intel/AMD was really strong back then.

I started using Sun workstations in the late 80s. I remember when their revenue reached $1b. I had a Sun on my desk as my dev machine for 7 years.

They, and the software that ran on it (Dataviews), and their customers (Westinghouse Software in my case) were all soon undone by the arrival of powerful commodity Wintel.

It's a good list, and it's supported by the anecdotal evidence from my own career: my first dev job after college was on Solaris, but that company moved away from Sun because of Sun DS.

Why do you think ZFS on MacOS would have helped in any significant way? AFAIK, and I may be wrong, but Apple doesn't have a history relying on OEMs for their software, especially something as critical as operating systems. Am I wrong? Was it different back then?

> Why do you think ZFS on MacOS would have helped in any significant way?

It would have bought Sun mind-share. In that time frame Sun was trying really hard to re-acquire mind-share it had lost to Linux due to the non-deal with Google, the brief cancellation of Solaris x86, etc. OpenSolaris was an attempt to rebuild mind-share. Was rebuilding mind-share enough? No, no way, but it was a start.

It could have led to Apple acquiring Sun, say.

> AFAIK, and I may be wrong, but Apple doesn't have a history relying on OEMs for their software, especially something as critical as operating systems. Am I wrong? Was it different back then?

Apple did the work of integrating ZFS into OS X. They believed in it. Steve Jobs wanted indemnification in light of the NetApp lawsuit. Jonathan wouldn't agree to it. Giving it could have been a betting-the-company event, but Sun needed that sort of thing.

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Do you remember "iPlanet", the "Sun Netscape Alliance"? Netscape's server software was pretty meh, if I recall.