iCloud drive errors on one Mac account

Question

I've been having problems trying to use iCloud Drive on my Mac. If I try to copy or move a file into iCloud Drive using Finder, I get an error -36. If I try to open a PDF that is already in iCloud Drive using Preview, I get an error message saying "Couldn’t communicate with a helper application." Numbers files give the same message. On the other hand, I can view the contents of text or PDF files in iCloud Drive using Quick Look, and I can copy a file into it using the ditto command in Terminal, and the file does get uploaded to the cloud.

After looking at some previous similar discussions, I tried turning off iCloud Drive syncing and turning it back on, but that didn't help.

I can access iCloud using the web interface, but I'd rather not.

I created another account on my Mac, and set it to use iCloud with the same Apple ID, and it works there fine. So whatever is messed up must be confined to my account. But where? I tried nuking various cache and preference files with "cloud" in their names, but no luck.

I'm using Ventura 13.6.9.

Same errors when booted in Safe Boot mode, same errors when back in normal mode.

I tried completely signing my Mac out of iCloud and signing back in. The errors persist.

The message about a "helper application" inspired me to look at Activity Monitor for related processes. I see that there is a process named com.apple.iCloudHelper belonging to the user account where iCloud Drive works, but no such process for the problematic account.

Running Console with com.apple.clouddocs in the search box for message text while triggering a -36 error produces:

default 14:43:55.792993-0700    runningboardd   Launch request for xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)> is using uid 501 (divined from auid 501 euid 501)
default 14:43:55.793081-0700    runningboardd   Executing launch request for xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)> (Launching extension com.apple.CloudDocs.iCloudDriveFileProvider(D8EE5FE4-6ECB-4E19-81D2-2508981E7155) for host 7753)
default 14:43:55.793117-0700    runningboardd   Checking PreventLaunch: global:0 exPath:/System/Library/PrivateFrameworks/CloudDocs.framework/PlugIns/com.apple.CloudDocs.iCloudDriveFileProvider.appex/Contents/MacOS/com.apple.CloudDocs.iCloudDriveFileProvider predicates:(null) allow:(null)
default 14:43:55.793165-0700    runningboardd   Creating and launching job for: xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
default 14:43:55.793340-0700    runningboardd   '(null)' Submitting extension overlay (context <RBSLaunchContext: 0x7ff740058090>):
<dictionary: 0x7ff74003e9f0> { count = 3, transaction: 0, voucher = 0x0, contents =
    (trimmed for size)
default 14:43:55.805349-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Memory Limits: active 0 inactive 0
 <private>
default 14:43:55.805392-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] This process will not be managed.
default 14:43:55.805418-0700    runningboardd   Now tracking process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]
default 14:43:55.805758-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] reported to RB as running
default 14:43:55.807219-0700    runningboardd   Acquiring assertion targeting [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] from originator [osservice<com.apple.FileProvider(501)>:7753] with description <RBSAssertionDescriptor| "com.apple.extension.session" ID:178-7753-5720 target:7964 attributes:[
    <RBSLegacyAttribute| requestedReason:ViewService reason:ViewService flags:( AllowIdleSleep PreventTaskSuspend PreventTaskThrottleDown )>,
    <RBSAcquisitionCompletionAttribute| policy:AfterValidation>
    ]>
default 14:43:55.807317-0700    runningboardd   Assertion 178-7753-5720 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]) will be created as active
default 14:43:55.808026-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring jetsam update because this process is not memory-managed
default 14:43:55.808068-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring suspend because this process is not lifecycle managed
default 14:43:55.808104-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring role changes because this process is not role managed
default 14:43:55.808136-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring GPU update because this process is not GPU managed
default 14:43:55.808202-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring memory limit update because this process is not memory-managed
default 14:43:55.810547-0700    fileproviderd   Hit the server for a process handle 7c6772900001f1c that resolved to: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]
default 14:43:55.814753-0700    secinitd    com.apple.CloudDocs.iCloudDriveFileProvider[7964]: root path for bundle "<private>" of main executable "<private>"
default 14:43:55.823057-0700    secinitd    AppSandboxUtilRealPathForUTF8StringPath(/System/Library/PrivateFrameworks/CloudDocs.framework/PlugIns/com.apple.CloudDocs.iCloudDriveFileProvider.appex)
default 14:43:55.828864-0700    secinitd    AppSandboxUtilRealPathForUTF8StringPath(/Volumes/Work/Users/jwwalker/Library/Containers/com.apple.CloudDocs.iCloudDriveFileProvider/Data)
default 14:43:55.830346-0700    secinitd    com.apple.CloudDocs.iCloudDriveFileProvider[7964]: AppSandbox request successful
default 14:43:55.834620-0700    containermanagerd   Using client sandbox path [<~~~>]; metadata = <<~~~>(2);<501/20/~~/0/1001>;uC761F768-E1A0-47EE-B476-7EC14BBB197D;pcom.apple.CloudDocs.iCloudDriveFileProvider;dp-1;uma(null);L0>
default 14:43:55.847044-0700    runningboardd   Setting client for [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] as ready
default 14:43:55.847537-0700    com.apple.CloudDocs.iCloudDriveFileProvider Identity resolved as xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
default 14:43:55.854887-0700    runningboardd   Invalidating assertion 178-7753-5720 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]) from originator [osservice<com.apple.FileProvider(501)>:7753]
default 14:43:55.855267-0700    runningboardd   Acquiring assertion targeting [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] from originator [osservice<com.apple.FileProvider(501)>:7753] with description <RBSAssertionDescriptor| "com.apple.extension.session" ID:178-7753-5721 target:7964 attributes:[
    <RBSLegacyAttribute| requestedReason:ViewService reason:ViewService flags:( AllowIdleSleep PreventTaskSuspend PreventTaskThrottleDown WantsForegroundResourcePriority )>,
    <RBSAcquisitionCompletionAttribute| policy:AfterValidation>
    ]>
default 14:43:55.855349-0700    runningboardd   Assertion 178-7753-5721 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]) will be created as active
default 14:43:55.855801-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring jetsam update because this process is not memory-managed
default 14:43:55.855842-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring suspend because this process is not lifecycle managed
default 14:43:55.855866-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring role changes because this process is not role managed
default 14:43:55.855889-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring GPU update because this process is not GPU managed
default 14:43:55.855930-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] Ignoring memory limit update because this process is not memory-managed
default 14:43:55.870681-0700    runningboardd   Invalidating assertion 178-7753-5721 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]) from originator [osservice<com.apple.FileProvider(501)>:7753]
default 14:43:55.870774-0700    runningboardd   XPC connection invalidated: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]
default 14:43:55.871601-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964] termination reported by launchd (0, 0, 256)
default 14:43:55.871673-0700    runningboardd   Removing process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]
default 14:43:55.871850-0700    runningboardd   Removing assertions for terminated process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964]
default 14:43:55.871928-0700    runningboardd   Removed last relative-start-date-defining assertion for process xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
default 14:43:55.895165-0700    runningboardd   Launch request for xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)> is using uid 501 (divined from auid 501 euid 501)
default 14:43:55.895240-0700    runningboardd   Executing launch request for xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)> (Launching extension com.apple.CloudDocs.iCloudDriveFileProvider(D8EE5FE4-6ECB-4E19-81D2-2508981E7155) for host 7753)
default 14:43:55.895270-0700    runningboardd   Checking PreventLaunch: global:0 exPath:/System/Library/PrivateFrameworks/CloudDocs.framework/PlugIns/com.apple.CloudDocs.iCloudDriveFileProvider.appex/Contents/MacOS/com.apple.CloudDocs.iCloudDriveFileProvider predicates:(null) allow:(null)
default 14:43:55.895384-0700    runningboardd   Creating and launching job for: xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
default 14:43:55.895659-0700    runningboardd   '(null)' Submitting extension overlay (context <RBSLaunchContext: 0x7ff73843e1e0>):
<dictionary: 0x7ff73f70a890> { count = 3, transaction: 0, voucher = 0x0, contents =
    (trimmed for size)
default 14:43:55.908735-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Memory Limits: active 0 inactive 0
 <private>
default 14:43:55.908818-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] This process will not be managed.
default 14:43:55.908883-0700    runningboardd   Now tracking process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]
default 14:43:55.909249-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] reported to RB as running
default 14:43:55.910732-0700    runningboardd   Acquiring assertion targeting [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] from originator [osservice<com.apple.FileProvider(501)>:7753] with description <RBSAssertionDescriptor| "com.apple.extension.session" ID:178-7753-5723 target:7965 attributes:[
    <RBSLegacyAttribute| requestedReason:ViewService reason:ViewService flags:( AllowIdleSleep PreventTaskSuspend PreventTaskThrottleDown )>,
    <RBSAcquisitionCompletionAttribute| policy:AfterValidation>
    ]>
default 14:43:55.910840-0700    runningboardd   Assertion 178-7753-5723 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]) will be created as active
default 14:43:55.911410-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring jetsam update because this process is not memory-managed
default 14:43:55.911448-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring suspend because this process is not lifecycle managed
default 14:43:55.911603-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring role changes because this process is not role managed
default 14:43:55.911796-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring GPU update because this process is not GPU managed
default 14:43:55.912101-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring memory limit update because this process is not memory-managed
default 14:43:55.915251-0700    fileproviderd   Hit the server for a process handle 5e7828500001f1d that resolved to: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]
default 14:43:55.917201-0700    secinitd    com.apple.CloudDocs.iCloudDriveFileProvider[7965]: root path for bundle "<private>" of main executable "<private>"
default 14:43:55.924221-0700    secinitd    AppSandboxUtilRealPathForUTF8StringPath(/System/Library/PrivateFrameworks/CloudDocs.framework/PlugIns/com.apple.CloudDocs.iCloudDriveFileProvider.appex)
default 14:43:55.928647-0700    secinitd    AppSandboxUtilRealPathForUTF8StringPath(/Volumes/Work/Users/jwwalker/Library/Containers/com.apple.CloudDocs.iCloudDriveFileProvider/Data)
default 14:43:55.930151-0700    secinitd    com.apple.CloudDocs.iCloudDriveFileProvider[7965]: AppSandbox request successful
default 14:43:55.934633-0700    containermanagerd   Using client sandbox path [<~~~>]; metadata = <<~~~>(2);<501/20/~~/0/1001>;uC761F768-E1A0-47EE-B476-7EC14BBB197D;pcom.apple.CloudDocs.iCloudDriveFileProvider;dp-1;uma(null);L0>
default 14:43:55.948535-0700    runningboardd   Setting client for [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] as ready
default 14:43:55.949438-0700    com.apple.CloudDocs.iCloudDriveFileProvider Identity resolved as xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
error   14:43:55.956657-0700    runningboardd   RBSStateCapture remove item called for untracked item 178-7753-5720 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964])
error   14:43:55.956712-0700    runningboardd   RBSStateCapture remove item called for untracked item 178-7753-5721 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7964])
default 14:43:55.960716-0700    runningboardd   Invalidating assertion 178-7753-5723 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]) from originator [osservice<com.apple.FileProvider(501)>:7753]
default 14:43:55.961103-0700    runningboardd   Acquiring assertion targeting [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] from originator [osservice<com.apple.FileProvider(501)>:7753] with description <RBSAssertionDescriptor| "com.apple.extension.session" ID:178-7753-5724 target:7965 attributes:[
    <RBSLegacyAttribute| requestedReason:ViewService reason:ViewService flags:( AllowIdleSleep PreventTaskSuspend PreventTaskThrottleDown WantsForegroundResourcePriority )>,
    <RBSAcquisitionCompletionAttribute| policy:AfterValidation>
    ]>
default 14:43:55.961190-0700    runningboardd   Assertion 178-7753-5724 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]) will be created as active
default 14:43:55.961682-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring jetsam update because this process is not memory-managed
default 14:43:55.961729-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring suspend because this process is not lifecycle managed
default 14:43:55.961751-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring role changes because this process is not role managed
default 14:43:55.961770-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring GPU update because this process is not GPU managed
default 14:43:55.961807-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] Ignoring memory limit update because this process is not memory-managed
default 14:43:55.983042-0700    runningboardd   Invalidating assertion 178-7753-5724 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]) from originator [osservice<com.apple.FileProvider(501)>:7753]
default 14:43:55.983144-0700    runningboardd   XPC connection invalidated: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]
default 14:43:55.984157-0700    runningboardd   [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965] termination reported by launchd (0, 0, 256)
default 14:43:55.984211-0700    runningboardd   Removing process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]
default 14:43:55.984417-0700    runningboardd   Removing assertions for terminated process: [xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965]
default 14:43:55.984483-0700    runningboardd   Removed last relative-start-date-defining assertion for process xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>
error   14:43:56.131131-0700    runningboardd   RBSStateCapture remove item called for untracked item 178-7753-5724 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965])
error   14:43:56.131270-0700    runningboardd   RBSStateCapture remove item called for untracked item 178-7753-5723 (target:[xpcservice<com.apple.CloudDocs.iCloudDriveFileProvider([osservice<com.apple.FileProvider(501)>:7753])(501)>:7965])

Answer 1

I seem to have solved my problem, albeit in an unsatisfying way. Having gotten tired of trashing a file here and there, I decided to move aside whole subfolders of ~/Library, while not logged into the problematic account:

~/Library/Application Support
~/Library/Containers
~/Library/Group Containers

Then when I logged in, the problem still existed. So I logged out and used another admin account to move some more folders aside:

~/Library/com.apple.icloud/searchpartyd
~/Library/Caches
~/Library/Daemon Containers
~/Library/Mobile Documents
~/Library/Preferences

At that point, the problem was gone! Then I started moving these folders back into place one at a time, logging in to test each time. And after I had moved all 8 folders back into place, iCloud Drive was still working. Cue "Twilight Zone" theme.