chasm

I do see the "I'll tap you when I'm ready" message from time to time (maybe once in 50, certainly not the problem you're having), but let me tell you what the problem is and a potential fix.

The reason for the difficulty is that your iPhone is trying or has connected to a non-working open Wi-Fi connection, and can't reach the internet to process some aspects of your request. The fix is to go into your iPhone settings -> Wi-Fi, and tell it to ask to connect to unknown networks (known networks will still be joined automatically). If there's a notoriously bad "known" network you've joined before that doesn't work (I have this problem in some parts of town with the carrier's hotspots), tell the iPhone to "forget" that network. This will cause your iPhone to rely on LTE data when you're not on a known-good Wi-Fi network, and thus the connection between your iPhone and the Watch will be stronger and thus Siri will work much more reliably. It made a huge difference for me, I hope it does the same for you.

Regarding pronunciation ... I agree that there could be more done in the area of fixing bad pronunciations, there is a way to correct names, here is the method I use to train it from scratch:

1. Ask Siri for the phone number of the name you know it will mispronounce.

2. After it says the name incorrectly aloud, say "that's not how you pronounce it."

It will then ask you to say the name, listen, and offer you choices of pronunciation. Select the one that is closest, and then it will pronouce it correctly next time.

I should add that although I now use an 802.11ac router supplied by my internet provider. I keep an Airport Express in my "presentation kit" when I do presentations to groups. Connect it to the ethernet and voila! A solid, dependable router that works flawlessly with AirPlay and doesn't suffer "lockdowns" the host company has put on their own Wi-Fi network (like blocking AirPlay, for example). Best router I have ever owned, bar none.

EdmontonGuy said:

I use Apple Maps when I travel but in Edmonton, Canada’s 5th largest metro Apple Maps sucks. No detail, no transit, no flyover.

Just for the record: Edmonton Alberta does in fact have loads of detail, it has full transit directions, and it has 3D satellite imagery (aka “flyover”). Maybe update your iPhone to iOS 12?

Reminder to commenters: under US law, trademark holders are required to vigorously (and yes, excessively) protect and defend their trademarks or risk losing control of them. This stems from Domino’s sugar failing to protect their logo until Domino’s Pizza was a huge national brand — and that’s why we have both today (even though I don’t think there was, or is, any consumer confusion with the two).

Apple literally has no choice but to threaten legal action against anything that even vaguely implies a similar mark or (worse) any possible endorsement. Don’t blame Apple for this one — this happens all the time between companies. Blame the courts for setting the precedent that even unrelated marks such be defended.

Quick example: “Pizzeria Uno” sued a Cuban restaurant called “Numero Uno” in Orlando FL — the latter having been around two decades earlier than Pizzeria Uno — and the Cuban restaurant lost. Would anyone in their right mind think Pizzeria Uno had opened one outlet of a Cuban restaurant? No. Did that help? No. And guess what was brought up as the precedent? Domino’s Pizza.

tzeshan said:

I cannot sync document folder between a MacBook Pro and an iMac through iCloud. What I may have done wrong? 

It’s not really anything to do with the topic, but the most likely reason is that we’re talking about two different document folders; one on each machine. The correct approach (if you wanna do this through iCloud) is to have one document folder: the one on iCloud. You then make aliases of that folder on your two machines. If it helps, you can rename the aliases to “iCloud document folder“ or something like that so that it is distinguishable from the mandatory Documents folder that you have in your user folder on both machines. Just put all the documents you want to be synced into the “iCloud documents folder“ on either machine, and it will always be in sync.

Another way to do this without using any cloud service is through programs such as Sync Two Folders (limited but free) and ChronoSync (powerful and an excellent value, but not free).