macOS 10.14.6 The request timed out

Yeah, that's not even slightly helpful. Blame the victim. I highly doubt there is any setting wrong for ANYONE that has this problem. We'd KNOW if the network wasn't connected. DNS seems the most likely culprit, but just that one site? With both Ethernet AND WiFi (They use separate addresses)? I tried Gigabit Ethernet, WiFI, even both at the same time. It makes no difference. Everything else works fine. Only Software Update is broken. The problem clearly is with Apple and their broken software. The only thing I can think to try is changing DNS servers a few times and hope one knows how to direct macOS to the correct place (assuming that has anything to do with it).

I had to manually install both of the last Mojave updates (the manual install will download just fine) and now Safari won't install either. App store updates for things from the Mac store install just fine, but it will NOT install ANYTHING via "software update" in preferences. It "times out" every single time. It doesn't even try to load (no progress at all). There must be some obscure setting in the OS install somewhere (old script; old something) from a previous OS version that Apple failed to wipe or whatever causing the issue, but because it doesn't happen to everyone it will probably never get fixed.

You might as well just tell people to do a clean install of macOS because I doubt anything else will work. It will otherwise probably be broken forever. NO ONE wants to do a clean install to fix something so utterly trivial. But with Apple anymore, this seems to be what you get.

Broken software.

Greetings StephenCPT,

Thank you for using Apple Support Communities. It seems like you are trying to update software, but you received an error about the connection timing out. Is there trouble connecting to the internet using Safari or other apps? How is the MacBook Air connecting to the internet? One thing you can do is to try and update macOS using a different Wi-Fi network. I would recommend you use this article to help troubleshoot the issue.

Recommended settings for Wi-Fi routers and access points

Please don't hesitate to let us know if the steps resolved your issue or if you need additional assistance.

Take care.

OK, FINALLY this problem was resolved for my iMac which is a late 2014 Mojave Version 10.4.6 with all the software updates. This problem started when a Security Update 2019-001 10.14.6 continued to give me this message "The request times out. An error occurred while installing the selected updates." So I thought it was a slow internet speed issue even using an ethernet connection, not WiFi. Even the Xfinity (my internet provider) Speed Test would not work and still does not, now that everything seems to be running correctly. Eau Rouge suggested I use this link https://support.apple.com/kb/DL2024?viewlocale=en_US&locale=en_US and after I installed it everything went back to normal! Lots of people seemed to have this problem so I thought the first security update which I mentioned in the beginning that would time out was corrupted.

I've had this problem for maybe 2 months. 10.14.6 just won't install.

I have fiber both home and at work, no problems there. Wifi with 0,5-1Gbps connection.

And, it says more that it times out during install?

I have iMac 2015. The autoupdate has failed for the last two months. So, i've tried to download it directly from Apple. This is the result. I've been using auto update for years and it's never given me this problem. All of a sudden, my system does meet the installation requirement? I don't think so. Without this update, I can't even upgrade to the latest Catalina.

James_User

Frustrated

I just bought an iMac about a week ago. I have the same problem. My internet is connected. There is a bigger issue. Now I can’t even update my apps because this software update won’t go through!!! Help please!!!

This problem is happening everywhere and I believe it is not a down load issue.

My iMac is using ethernet and downloads everything else except this security update

I believe the update is the culprit!

Any solutions?

I've had this for all major updates. And then I got it for the Catalina update. Worked around the problem by reinstalling Catalina from Recovery instead. When I got the first major update after that, it worked.

I'll give it a try, but I'm pretty sure I never had any failed previous updates as I converted from El Capitain to 10.14.5 directly. It's possible it might not even let me install the update if it was already in the 10.14.5 upgrade.

EDIT: This worked. A Safari update appeared and it was able to download and install it. I see Catalina waiting as well (no interest at the current time due to loss of 32-bit app capability). Good job!

Actually... Broken company. This degradation in software quality is so widespread now.

My input here: I have the same problem. I had two such failing updates. Security-Update 2019-002 for Mojave, and Safari 13.0.4

I was lucky to find (thank Google - Apple's site is no help) the link to download the security update installer manually. So I did, and installed without a hitch --- this means, that the "network issue" is just plain wrong. Safari was perfectly able to download the same thing from Apple.

As for the Safari update -- I'm stumped, since I could not find any link to download it manually. the problem lingers on, and I just have nowhere to get the software from.

My suspicion is that this is yet another trick to "persuade" us users to "upgrade" to 10.15 (Catalina) and so lose about all our beloved, well-functioning old Mac software (which happens to be 32bit). I'm a Mac and iOS developer, and I have thousands of $ invested in great software tools - so I will never upgrade to 10.15. Not until all these tools become obsolete themselves.

Anyway, Apple software (even system software) is now failing hundreds of times a day. One can just open the console and browse the endless list of crashes, exceptions and other failures throughout the system to confirm this.

Yet another note on the unhelpful piece of advice. I have both MacBookPro (15" 2017) and an iMac (27" late 2015) both run MacOS 10.14.6 and all updates applied. On the same very WiFi at home - one continuously fails to download and install the security update 2019-002 and Safari 13 update - showing with the above message, while the MBP had no problems at all, downloaded, and installed the same updates at the same time.

So sending us to verify network configuration is not only unhelpful, it is time-consuming and futile. Maybe supporters should dig just a little deeper before advising.

I have the same problem.

thank you, this solved my problem too

Thank you @Joeychin!! that worked!!

This was helpful. Thank you !!!