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Howard Oakley (via the Michael Tsai Blog) said:
iCloud Drive Breaks the macOS Command Line

Apple’s current engineering solution breaks consistency of file names and paths. When a file has been evicted from local storage, and only exists in full in iCloud storage, the local stub file uses the previous name prefixed with a stop/period, and gains the extension of .icloud. When that file is downloaded to local storage – something which can be triggered by all sorts of events – the leading stop/period and the extension are stripped.
[…]
Many commands and scripts can safely ignore files which the user has placed in their iCloud Drive. But the moment that a user enables Desktop & Document Folders to be stored in iCloud, with Optimize Mac Storage enabled, file names in ~/Documents are affected, and commands and scripts will fail when run on one of the most important and active directories on most macOS systems.
[…]
Apple’s own most robust tool for locating files, the Finder alias, is broken by iCloud.
[…]
Inevitably, all hard and symbolic links made to evicted files are also broken by their eviction.

Faced with the problems posed by iCloud, a lot of commands, shell scripts and other scripting becomes inordinately complex, and in some cases impossible. Apple needs to continue to evolve the iCloud interface, making it consistent with the fundamental needs of commands and shell scripts. If it doesn’t, but continues to converge with iOS, it will undermine macOS itself.
Ugh, what a mess.

Now that it's been mentioned, I'm not too surprised, but I would have hoped that Apple could implement "Optimize Mac Storage" in a way that doesn't break the command line.

It's definitely possible to do this. I'm thinking that it would be easiest to do it using some kind of network file system like the old Andrew File System. For those who don't know, AFS is/was a network file system designed for wide-area/slow connections. The file system would be mounted, much like any other remote volume, but it would cache the files locally for faster access to commonly-accessed files.

Instead of Apple's existing mechanism (where it replaces offloaded files with a special kind of iCloud alias that causes the file to be re-downloaded when accessed via the Mac-style (but apparently not UNIX-style) APIs), they could have implemented this by replacing your Documents folder with a mount-point for an AFS-like file system, which can download files from iCloud as needed and purge them at later times. You wouldn't be able to hard-link to these files (because it's a different volume), but you could have symlinks to this volume and scripts would continue working because all of the filenames would remain valid (triggering downloads as necessary to access the content).

If anyone from Apple is reading this, please forward this message to whoever is responsible for this feature. There is a better way to do what you're trying to do and Apple should migrate to it as soon as it is practical to do so.
 
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If anyone from Apple is reading this, please forward this message to whoever is responsible for this feature. There is a better way to do what you're trying to do and Apple should migrate to it as soon as it is practical to do so.
Around 2001, I was part of a rather ad hoc/informal effort to support OpenAFS in MacOS. I describe it that way because ultimately my skills were ill-suited for the role I was asked to perform - you could say I was simply the wrong person in the right place. As I recall, the interest initially came from Apple itself.

I actually met with some Apple kernel developers as part of my work, but frankly was overwhelmed and somewhat in awe of their expertise. While I was able to demonstrate OpenAFS worked on MacOS, others had to advocate for its usage, or refine its behavior, because I could do neither. In hindsight, I suspect that others may have expected me to do both.

Whether Apple lost interest due to my shortcomings or lack of effort on their part to ensure an investigation was properly done, or they actually learned it didn't suit their goals at the time, I can't say. But I do have to wonder if that effort had gone differently, perhaps OpenAFS would be used in MacOS already.
 


What I would like to see in macOS is better caching / serving up of directory structures to make traversal a lot quicker. I'm flummoxed that it can take up to ten seconds for a 2nd- or 3rd-level directory's contents to come up, even with a 10GBe connection to a otherwise-unused NAS. I'm not talking thousands of files either.

Moreover, it would be great if macOS could give an indication whether it's still working on serving up directory contents or whether it has finished that task and that the directory is empty. In Sierra, there is no such indication, so a directory may appear empty because the system is still looking, because the user lacks privileges, or because it's actually empty. macOS gives the user zero means of differentiating among the three.
 


What I would like to see in macOS is better caching / serving up of directory structures to make traversal a lot quicker. I'm flummoxed that it can take up to ten seconds for a 2nd- or 3rd-level directory's contents to come up, even with a 10GBe connection to a otherwise-unused NAS. I'm not talking thousands of files either.

Moreover, it would be great if macOS could give an indication whether it's still working on serving up directory contents or whether it has finished that task and that the directory is empty. In Sierra, there is no such indication, so a directory may appear empty because the system is still looking, because the user lacks privileges, or because it's actually empty. macOS gives the user zero means of differentiating among the three.
I found disabling caching for SMB actually improves behaviour with my NAS (at home and work).
Instructions here: https://support.apple.com/en-ca/HT207520

in Sierra, when it's still loading/reading the directory, you should get a spinning gear icon in the bottom right of a Finder window. The only possible sign of a permissions issue is if you get the "no write" icon in the bottom left of the status bar. Both of these are only if the "Status Bar" is set to be shown (from the View menu in the Finder, "Show Status Bar"), which should be on by default but isn't for the past few macOS versions, which then gives the described problem of giving the user no feedback - just a blank window.
 


I found disabling caching for SMB actually improves behaviour with my NAS (at home and work).
Instructions here: https://support.apple.com/en-ca/HT207520
[snip]
A few years back, I switched from Finder to Path Finder (https://cocoatech.com/#/) and lost most of the Finder's problems. It has an option to quit Finder when it starts, and has its own desktop, plus editable contextual menus, and and and. And of course, they have a trial period, I think it's 30 days. Have fun.
 


What I would like to see in macOS is better caching / serving up of directory structures to make traversal a lot quicker. I'm flummoxed that it can take up to ten seconds for a 2nd- or 3rd-level directory's contents to come up, even with a 10GBe connection to a otherwise-unused NAS. I'm not talking thousands of files either.

Moreover, it would be great if macOS could give an indication whether it's still working on serving up directory contents or whether it has finished that task and that the directory is empty. In Sierra, there is no such indication, so a directory may appear empty because the system is still looking, because the user lacks privileges, or because it's actually empty. macOS gives the user zero means of differentiating among the three.
It’s terrible. I have a 120TB home NAS4Free server. However there is one amazing fix:

Turn off Icon Preview on all server shares. (Finder preferences or View preferences.) Makes all the difference in the world.

Another fix that helps, but to a lesser extent, is [avoiding] calculate all sizes. However this information is kind of useful and the calculation seems to happen in the background and doesn’t impact the Finder too adversely.

FYI, I still use AFP for my shares.
 
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macOS is also terrible at searching shares. I use NeoFinder to catalog and search all
my shares and drives. It's amazing, fast, makes thumbnails, its database can be used with many clients with a server version of the software, it’s well supported by the developer, and it's very affordable. One note if you do decide to use NeoFinder, it recently was given the feature to edit the Finder from within NeoFinder, meaning you can change file names and or delete files. That is a feature I fear, but you can turn it off via Terminal, and the instructions are on their website.

I used Path Finder a few years ago, and it also was very good, but it also had some funky bugs that I didn’t like, especially with shared drives. Nothing horrible but eroded my confidence in the program just enough that I stopped using it.

*I don’t work for NeoFnder. Just one of these pieces of software that just works.
 
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I just updated my two Macs to macOS 10.13.5. On one, the ability to synch iMessage in the iCloud is available through preferences, not on the other Mac. Have rebooted without success. Both say current version is 11.0 (5500). Any suggestions on how to update Messages?
 


Now, two of three Macs (a late 2012 Mini and a 2017 27" iMac) have not upgraded Messages... and I've checked to see that 10.13.5 is shown as the new system.
 


I have a problem.

After updating my various Macs to macOS 10.13.5, I tried to invoke the "Messages in iClouds" feature. From some other websites, all they say to do is the following:

1. In Messages, open the Preferences pane.
2. Under the Accounts tab, place a check mark (tick mark) in the line called "Messages in iCloud" line.

For me, I don't see that line....
 


I have a problem.
After updating my various Macs to macOS 10.13.5, I tried to invoke the "Messages in iClouds" feature. From some other websites, all they say to do is the following:
1. In Messages, open the Preferences pane.
2. Under the Accounts tab, place a check mark (tick mark) in the line called "Messages in iCloud" line.
For me, I don't see that line....
Also with the update, you can't avoid the 'do you want to delete the message' alert by using the option key.
 


To enable "Messages in iCloud", I had to log out of iCloud then log back in. I've always had problems after a system update where it puts up a message saying it had a problem logging in to iCloud, then I lose the text message capability of Messages on my Mac. I expect the same with 10.13.6 and "Messages in iCloud" when it comes out.
 


To enable "Messages in iCloud", I had to log out of iCloud then log back in. I've always had problems after a system update where it puts up a message saying it had a problem logging in to iCloud, then I lose the text message capability of Messages on my Mac. I expect the same with 10.13.6 and "Messages in iCloud" when it comes out.
Thank you - logging out of iCloud and back in caused the Enable option to appear!
 


To fix an issue, I disconnected my iCloud Drive on my Mac from the iCloud. A directory 'iCloud Drive (Archive)' was created from the old iCloud. When I reconnected to iCloud, the iCloud Drive icon is missing from my home directory and I have not been able to restore it. I have the listing in the Finder Sidebar farorites, but not in any directory listing shown by the Finder.

I'm aware the actual location is '~/Library/Mobile Documents/com~apple~CloudDocs' so I can access it by putting a symbolic link in my home directory. If I create the symlink and change the name it iCloud Drive, access works but it does not get the special icon Apple provides (I'm aware that I can change that with the Finder's Get Info). I have been unable to find any documentation on this problem. Repeating the disconnect of the iCloud driver from Preferences -> iCloud as well as moving, renaming, or deleting the iCloud Drive (Archive) file has not tricked the OS into restoring the reference and special icon.

Ideas? Just want this machine to match the other machines I own. OS is 10.13.6. I was running 10.13.5. MacBook Pro (Retina, 13-inch, Early 2015).
 


I have run into a strange issue with sending an email through the iCloud servers. I had an email with a 28-page attachment, either in Word or as a PDF (less than a MB in size), that I would try to email. The Mail program on my Mac said it sent, but the recipients never got them. I solved the near-term problem by putting them in my Dropbox and sending them the link but then spent a bunch of time trying to figure out why. I tried sending the email to myself under different circumstances, making docs smaller, zipping them, sending through the iCloud website using Safari, and other things. Got on the phone with Apple Support to try to solve it, too.

I finally found that if my email included a reference to the website of a certain college religious organization (utbaptist.org), the email would go into the void. The reference could be in the subject, the text, in an attachment, even a zipped attachment. I could send the same email from my Gmail account to my iCloud account, but not the other way around. The Apple Support person tried from his iCloud account and had the same problem.

Any ideas on what's going on? I thought it might be iCloud's "silent filtering", but that would be on incoming emails, not outgoing. Since I get no warning when it doesn't send, I worry about running into this problem again.
 


I have been unsuccessful working with Apple on the same issue. I write for a law-enforcement website and from what I can tell, certain words in a Microsoft Word attachment cause my email to go silently into the bit bucket.

Rather than accept that this is an iCloud issue, they instead are focusing on my iPhone, iPad, and Mac Pro as the culprits, asking me to run diagnostic after diagnostic, and wipe and reinstall the OS.
 


Rather than accept that this is an iCloud issue, they instead are focusing on my iPhone, iPad, and Mac Pro as the culprits, asking me to run diagnostic after diagnostic, and wipe and reinstall the OS.
Exactly the type of run-around I've gotten from Apple about other issues that are definitively bugs - blame something, anything else, but under no circumstance admit this might potentially, possibly be an actual bug that needs fixing!
 


I have been unsuccessful working with Apple on the same issue. I write for a law-enforcement website and from what I can tell, certain words in a MS-Word attachment cause my email to go silently into the bit bucket.
Rather than accept that this is an iCloud issue, they instead are focusing on my iPhone, iPad, and Mac Pro as the culprits, asking me to run diagnostic after diagnostic, and wipe and reinstall the OS.
I tried sending to my Gmail from iCloud in Apple Mail - you are right. If I include "utbaptist.org" in the text of the email, it never shows up. I tried it from a different Gmail account (wife's) with "utbaptist.org", and it sent fine to my Gmail from her Gmail, so it isn't being filtered on the Gmail end. I tried the same thing from my iPhone (iOS 12), same results. It never shows up.

So, I went to iCloud.com, logged in and tried it, too - never showed up. (Or at least it hasn't yet after an hour and all the other ones have - didn't go in spam either.)

Strange that Apple is filtering outgoing mail. (I didn't check if other Baptist-related organizations are being filtered.)
 


Ric Ford

MacInTouch
I finally found that if my email included a reference to the website of a certain college religious organization (utbaptist.org), the email would go into the void.
Wondering if there were something like malware involved, I checked the website with three different checkers* and didn't see any issues reported, nor does it trigger other malware checks I use routinely.

*VirusTotal, NetCraft, and Cisco/Talos
 


Wondering if there were something like malware involved, I checked the website with three different checkers* and didn't see any issues reported, nor does it trigger other malware checks I use routinely.
*VirusTotal, NetCraft, and Cisco/Talos
As a security guy for a large higher-ed institution, I can tell you that blacklists and whitelists for email websites are very much an art, not a science. Many times we have users put an innocuous URL in an email, only to find that one of the sites we pay to get notified of emerging threats doesn't like it, and it just silently vanishes. And there are many such lists....
 


Wondering if there were something like malware involved, I checked the website with three different checkers* and didn't see any issues reported, nor does it trigger other malware checks I use routinely.

*VirusTotal, NetCraft, and Cisco/Talos
I have seen things like this happen when a domain gets put on some naughty list; the domain or mail server gets hacked, or some other server under their domain becomes a control center for some malware, and the domain gets a bad reputation and becomes a keyword, and then it's toast ,as far as the blacklist that is in use. Those lists are sometimes only on the server (for example, if someone spammed 100k addresses through iCloud using that domain, only Apple may have blacklisted it).

Having someone from utbaptist.org (preferably their email admin) reach out to Apple might be more fruitful.
 


I tried sending to my Gmail from iCloud in Apple Mail - you are right. If I include "utbaptist.org" in the text of the email, it never shows up. I tried it from a different Gmail account (wife's) with "utbaptist.org", and it sent fine to my Gmail from her Gmail, so it isn't being filtered on the Gmail end. I tried the same thing from my iPhone (iOS 12), same results. It never shows up. So, I went to iCloud.com, logged in and tried it, too - never showed up. (Or at least it hasn't yet after an hour and all the other ones have - didn't go in spam either.) Strange that Apple is filtering outgoing mail. (I didn't check if other Baptist-related organizations are being filtered.)
Thanks for checking. Shows I'm not crazy or doing something wrong.

In order to keep it all in the iCloud sphere I send from the address xxx@mac.com to my address xxx@me.com. These are the same mailbox, all within Apple's control. The support person had never seen the problem before; his thought was that the website had some sort of permission block for sending, but that makes no sense to me. He suggested I make a screen video of the action to send in, but we were heading out of town and he had already confirmed the problem, so I didn't see the urgency.

The problem first showed up on an email I sent in late August but didn't realize it was disappearing in the cloud until last week.
 


I have seen things like this happen when a domain gets put on some naughty list; the domain or mail server gets hacked, or some other server under their domain becomes a control center for some malware, and the domain gets a bad reputation and becomes a keyword, and then it's toast ,as far as the blacklist that is in use. Those lists are sometimes only on the server (for example, if someone spammed 100k addresses through iCloud using that domain, only Apple may have blacklisted it). Having someone from utbaptist.org (preferably their email admin) reach out to Apple might be more fruitful.
We texted them to let them know of the problem, and they said they'd check into it. Its staff is only a couple of ministers and an admin, and they don't even use utbaptist.org in their email address, so not sure why it would be on the "naughty list". And if it were, wouldn't it have been blocked on the incoming email from Gmail? Strange!
 


Curious, I just put the magic word in a test message and sent it from my Gmail to my iCloud address and got the following bounce message:
The response from the remote server was:
550 5.7.1 [CS01] Message rejected due to local policy. Please visit https://support.apple.com/en-us/HT204137
That looks to me like blacklisting that Apple is using on their end. It's plausible that something got hacked or that the blacklisting screwed up. There are multiple blacklists out there, and different servers use different ones. The utbaptist.org web site says it's "powered by Weebly," so they should ask Weebly for help.
 


I have seen things like this happen when a domain gets put on some naughty list; the domain or mail server gets hacked, or some other server under their domain becomes a control center for some malware, and the domain gets a bad reputation and becomes a keyword, and then it's toast ,as far as the blacklist that is in use. Those lists are sometimes only on the server (for example, if someone spammed 100k addresses through iCloud using that domain, only Apple may have blacklisted it).
Yes, this happened to me back in March of this year. My main web business domain got blacklisted by no fault of my own, and my hosting company not only blocked my newsletters from sending, but even blocked my normal email sent from the same domain. It took a few days to get this figured out, but I ultimately had to contact a company called Cloudmark and get my domain removed from their list. Once I did contact them, it took about an hour for them to fix this. Evidently, lots of innocent web businesses get caught up due to spammers using their domain address to spam.

Here's what they state:
Why is Cloudmark blocking my messages?
Cloudmark Sender Intelligence (CSI) is a service that provides data about the reputations of message-sending servers to messaging service providers. The data indicates which servers usually send spam and which ones usually send legitimate messages. Data about some servers may be ambiguous.

Different service providers have different policies about what to do with CSI's data, especially about how to interpret reputations that are ambiguous. Cloudmark is not a messaging service provider and does not block your messages, but your service provider may choose to do so.
I wasted a ton of time checking for the "spamminess" of my newsletters, but they always came out clean. Here's a few I used to check-
I don't know if this will help you, but it might help someone.
 


As a security guy for a large higher-ed institution, I can tell you that blacklists and whitelists for email websites are very much an art, not a science. Many times we have users put an innocuous URL in an email, only to find that one of the sites we pay to get notified of emerging threats doesn't like it, and it just silently vanishes. And there are many such lists....
Does the same (or similar) thing apply to ftp?

My accountant has his own ftp page/facility but every time I try to send him my annual accounts (5 Quicken Windows files plus many pdfs etc totalling about 400MB) he gets an empty zipped file. He runs nothing but Windows, so I use Quicken Windows running under Parallels Desktop, not Quicken Mac (which I don't think is available here in Australia anyway).

I've tried all sorts of combinations of zipping on the Mac and in Windows, sending from the Mac side and from the Windows side, etc, but nothing works. I know my Mac-zipped file is OK because if I burn it to CD and post it to him, he can use it. He has many other clients who successfully use his ftp facility. I and one other client are the only ones who are unsuccessful.

Ideas, comments, suggestions will be gratefully received.
 


Ric Ford

MacInTouch
My accountant has his own ftp page/facility but every time I try to send him my annual accounts (5 Quicken Windows files plus many pdfs etc totalling about 400MB) he gets an empty zipped file.
BetterZip works for making 7zip-encoded, Windows-compatible file archives but it doesn’t send them. Dropbox should work, and there are a ton of FTP programs. I like Cyberduck and also use Transmit.
 


Yes, this happened to me back in March of this year. My main web business domain got blacklisted by no fault of my own, and my hosting company not only blocked my newsletters from sending, but even blocked my normal email sent from the same domain. It took a few days to get this figured out, but I ultimately had to contact a company called Cloudmark and get my domain removed from their list. Once I did contact them, it took about an hour for them to fix this. Evidently, lots of innocent web businesses get caught up due to spammers using their domain address to spam.
Why did your hosting company block you rather than try to help you? Were they claiming you had violated their terms of service?

The few times I have run into blacklisting problems over the past decade or so, I contacted my hosting company and they dealt with it or told me what I need to do to deal with it. That's part of what I pay them for. I ran into blacklisting repeatedly with an earlier hosting company and eventually found out the problem was that they were hosting spammers running from the same or similarly numbered servers. At that point I changed hosting companies and incidents became rare.
 


Does the same (or similar) thing apply to ftp?
My accountant has his own ftp page/facility but every time I try to send him my annual accounts (5 Quicken Windows files plus many pdfs etc totalling about 400MB) he gets an empty zipped file. He runs nothing but Windows, so I use Quicken Windows running under Parallels Desktop, not Quicken Mac (which I don't think is available here in Australia anyway).
I've tried all sorts of combinations of zipping on the Mac and in Windows, sending from the Mac side and from the Windows side, etc, but nothing works. I know my Mac-zipped file is OK because if I burn it to CD and post it to him, he can use it. He has many other clients who successfully use his ftp facility. I and one other client are the only ones who are unsuccessful.
Ideas, comments, suggestions will be gratefully received.
Others will have better ideas regarding the empty zipped files. I do know that, based on my experience, zipped files are routinely rejected by much multi-user security software, such as used for small businesses, institutions, and governments. Our state government bans the use of Dropbox or the use of Dropbox links. They have their own version of Dropbox, which is really a pain to use. Sometimes it is just simpler to drop a flash drive in the mail.
 


Why did your hosting company block you rather than try to help you? Were they claiming you had violated their terms of service?
Their servers were automatically set up to to block when there was a CSI "violation". Once this was escalated to senior support, they told me what the issue was. Evidently, this was not very common for them. I guess I am one of the few customers who sends out a big emailing list. Most people/companies these days use a 3rd-party company to do that, but I use a program called PHPList and do it myself to save money.
 


Any ideas on what's going on? I thought it might be iCloud's "silent filtering", but that would be on incoming emails, not outgoing.
I have seen before that iCloud does spam filtering on outgoing messages. I've even had it decide to eat all messages sent to my own external email address.
 



I tried sending to my Gmail from iCloud in Apple Mail - you are right. If I include "utbaptist.org" in the text of the email, it never shows up. I tried it from a different Gmail account (wife's) with "utbaptist.org", and it sent fine to my Gmail from her Gmail, so it isn't being filtered on the Gmail end. I tried the same thing from my iPhone (iOS 12), same results. It never shows up.
So, I went to iCloud.com, logged in and tried it, too - never showed up. (Or at least it hasn't yet after an hour and all the other ones have - didn't go in spam either.)
Strange that Apple is filtering outgoing mail. (I didn't check if other Baptist-related organizations are being filtered.)
I just tried this, both from my iCloud account to my Google business account and in the other direction. With the word test in the subject line and If I include "utbaptist.org" in the text of the email, it never shows up. [in the body], the email goes through immediately.

Whatever is causing it, it's not system-wide.

I've seen silent non-delivery problems from iCloud in the past. The "secure message" service my bank uses sends email notifications. Those notifications never arrive when sent to my @mac.com account, but work fine when sent to my personal Gmail account. This has been consistently the case for years.

Odd.
 


Their servers were automatically set up to to block when there was a CSI "violation". Once this was escalated to senior support, they told me what the issue was. Evidently, this was not very common for them. I guess I am one of the few customers who sends out a big emailing list. Most people/companies these days use a 3rd-party company to do that, but I use a program called PHPList and do it myself to save money.
Many hosting companies tend to limit the use of mailing lists, forcing people to use services like MailChimp, but other servers may flag the mailing list companies as spammers.
 


I just tried this, both from my iCloud account to my Google business account and in the other direction. With the word test in the subject line and If I include "utbaptist.org" in the text of the email, it never shows up. [in the body], the email goes through immediately.
Thanks for letting me know it worked for you. I just tried sending the term again and now it is working! The power of MacInTouch at work, or else the organization was able to get through to Apple.
 


Many hosting companies tend to limit the use of mailing lists, forcing people to use services like MailChimp, but other servers may flag the mailing list companies as spammers.
Yes, true on all accounts. I've been with my hosting company, Tierra.net, for about 15-20 years now and have about 10 sites with them. One of the senior tech support specialists is a friend and he always gives me the straight poop on what's going on. Everything that you stated is what he told me.

I have to be very, very careful now as to who gets added to the list. I believe what happened was that bots added a bunch of stolen addresses to the list (before I was really paying attention) and caused those users to add me as spam. I have a system set up now so that it's next to impossible now for this to happen, but I am very careful.
 


I switched to FastMail after having the same types of problems with Godaddy's email.

Godaddy would intermittently lose emails from squareup.com, my payment processor, and two brokerages, including tdameritrade.com. These are not shady domains. Never being sure whether important emails would get through was an enormous problem. Their technical support was sympathetic but unable/unwilling to solve the problem - they admitted that whole domains are rejected via blacklists before emails ever reach user accounts.

In contrast, FastMail knows their stuff. I was able to reduce three mailboxes into one by using subfolders. Their spam control is logical, effective, and configurable. And FastMail competently imported 170 email forwards from an exported text file. Having dependable email has been well worth $50/year.

BTW, at the same time I switched web hosting over to Dreamhost and now pay less in total than I once did to Godaddy.
 


Messages app on Mac unable to sync with iCloud:

My lovely bride finally acceded to my advice that if you have to send a long text, it's easier doing so from her MacBook Pro keyboard than via her iPhone 7 soft keyboard. Unfortunately for me, it didn't work!

We are unable to get Messages on her laptop to sync up with her iPhone/iCloud account. Even more baffling, my High Sierra Messages app preferences have the checkbox for synching with iCloud, but her High Sierra Messages app does not (see screen shots linked below).

I've spent several hours attempting to figure this out, up to and including re-applying the macOS 10.13.6 Combo updater, with no luck. She is signed into her iCloud account, and her contacts are shared between Mac and iPhone. Any tips or clues as to what else I can check would be most appreciated.
 


Messages app on Mac unable to sync with iCloud:

We are unable to get Messages on her laptop to sync up with her iPhone/iCloud account. Even more baffling, my High Sierra Messages app preferences have the checkbox for synching with iCloud, but her High Sierra Messages app does not (see screen shots linked below).
My experience exactly mirrors yours. On my iMac, my account has the messages in iCloud checkbox and hers does not. Wish I had the answer for you (and myself).
 


Messages app on Mac unable to sync with iCloud:

My lovely bride finally acceded to my advice that if you have to send a long text, it's easier doing so from her MacBook Pro keyboard than via her iPhone 7 soft keyboard. Unfortunately for me, it didn't work!

We are unable to get Messages on her laptop to sync up with her iPhone/iCloud account. Even more baffling, my High Sierra Messages app preferences have the checkbox for synching with iCloud, but her High Sierra Messages app does not (see screen shots linked below).

I've spent several hours attempting to figure this out, up to and including re-applying the macOS 10.13.6 Combo updater, with no luck. She is signed into her iCloud account, and her contacts are shared between Mac and iPhone. Any tips or clues as to what else I can check would be most appreciated.
Did you try logging her out of iCloud, then back in? I don't know if it will fix the problem, but it has fixed other odd problems for me in the past.
 


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