Synchronisation woes with macOS Mail.app Signatures

This blog post applies to macOS 12 (Monterey), other versions may differ.

It used to be that setting up a new computer involved the difficult choice of spending hours tweaking settings and trying to remember what arcane incantations were required to obtain the perfect setup, or cloning your old computer and importing years of cruft which quickly removed much of the sheen and speed. To its credit, Apple have been quietly chipping away at the configuration synchronisation for many years now, with Mail settings such as accounts, signatures and rules magically appearing on a new machine when you set it up. Typical of Apple’s slow-but-steady approach, it turns out that for Mail this is actually achieved via iCloud Drive so it is to some extent controllable via the toggle in Preferences➡Apple ID➡iCloud Drive➡Mail.

One reason that developers shy away from synchronisation is that it is a feature fraught with edge cases that make it deceptively hard to do reliably, and unreliable synchronisation is worse than none, at best leading to head scratching frustration and worse, loss of data. This was illustrated to me when my email signatures were failing to appear on a newly configured Mac. I was happy to import them manually but locating the correct place to put them was hard to track down, and iCloud Drive synchronisation meant that it took many attempts to get everything working.

The symptom of the problem was that all my accounts were showing up with 0 signatures. Moreover when I added one manually, it would disappear as soon as I quit Mail. iCloud Drive appeared to be working correctly, with all my other files present. In hindsight I suspect the download process was stuck but iCloud remains frustratingly opaque to troubleshoot and when even a reboot could not persuade the missing files to appear, it was time to attempt surgery.

Confusingly, Mail configuration is stored in multiple places. After much trial and error, my conclusion is that the iCloud synchronised files live in Library/Mobile\ Documents/com\~apple\~mail/Data/V4/Signatures/ (all paths relative to your home directory unless otherwise stated). However adding files to this directory did not fix the problem and at one point I tried deleting this directory and that deletion synchronised to another computer–be warned ⚠️ (Thank goodness for Time Machine backups.)

I was finally able to make signatures work again on the errant Mac by shutting down Mail, and then adding them to Library/Mail/V9/MailData/Signatures/. I believe I also disabled Mail in iCloud Drive but then I restored it afterwards and it did not complain. However on the second Mac where iCloud Drive copied down bad data, any files added to Library/Mail/V9/MailData/Signatures/ were removed the next time Mail started if Mail was enabled in iCloud Drive. Trying to convince iCloud this was a file newer than the server copy by editing the .plist file did not work. This was eventually fixed by copying the contents of Library/Mail/V9/MailData/Signatures/ to Library/Mobile\ Documents/com\~apple\~mail/Data/V4/Signatures/ and re-enabling Mail in iCloud Drive.

And so our tale of synchronisation woe has a happy ending. Credit to Apple for continuing to use text files for configuration, the ability to manipulate these via the terminal and easily restore them from a Time Machine backup were crucial to the successful outcome.

Apple News+ (UK) – A Review

Having caught up on my backlog of reading during lockdown, I decided to accept Apple’s offer of a free trial of their News+ service. The concept seems attractive for someone who would like to read widely without the great investment of time and money needed to take individual subscriptions to many publications. Unfortunately as I near the end of my month-long trial, I do not intend to continue with it.

The News+ “anchor-tenant” for current affairs in the UK is The Times. It had been my expectation that I could open the News+ app every day and peruse a digital newspaper, with all the in-depth articles and quality journalism that one gets that is so often missing from the 24/7 Internet news cycle. However the News+ service just seemed to give me access to a selection of online stories from The Times, with little to differentiate this offering from non-News+ providers such as The Evening Standard, The Independent or BBC News.

Some of these aforementioned providers have very aggressive advertising on their websites so even an advert-free reading experience would have potentially been a benefit, except News+ continues to display adverts, mostly terrible ones, in a way that seemed to maximise the interruption to the reading experience. In contrast, The Guardian app has the option to remove all adverts for £5.99 per month.

News+ also offer a selection of electronic magazines on a wide variety of topics. Some of these magazines are natively formatted for the app which offers a pleasing reading experience on screens both large and small (such as a phone). Sadly the majority I am interested in are just PDFs. Many local libraries (including my own) already offer free access to e-magazine services that include what are termed digital replicas of paper magazines so there is little incentive to subscribe just for the magazines.

MacOS Keyboard Shortcuts for Terminal Users

Despite its reputation for flashy graphics, macOS has a number of nifty features and shortcuts for terminal users. Here are some of my favourite keyboard shortcuts within the Terminal application itself:

  • ⇧⌘a (“shift-cmd-a”) to copy the output of the last command.
  • ⇧⌘v (“shift-cmd-v”) to paste the currently selected text.
  • ⌃⌘v (“control-cmd-v”) to paste escaped text.

The following keyboard shortcuts work in other applications:

  • ⌥⌘c (“option-cmd-c”) in Finder will copy the path to the selected file(s) (via @scriptingosx).
  • ⇧⌘. (“shift-cmd-fullstop”) toggles show hidden files, even in file open/save dialogs (via @howardnoakley).
  • ⌃t (“control-t”) transposes the two characters to the left of the cursor (via @eWhizz).

While testing the copy & paste shortcuts in this post, I also discovered—after 15 years of being a Mac user—that Finder has the ability to show the current contents of the clipboard (Edit→Show Clipboard).

MacOS External Storage Setup

A combination of a growing volume of personal media from 24+ megapixel cameras/4k HD video-recording phones, the switch to smaller solid-state internal drives, and the increasing life-span of our desktop computers, means that at some point you are likely to find yourself needing to offload data to an external storage device. Having gone down this path earlier in the year I thought I would share my experiences with the WD My Book Duo.

Continue reading “MacOS External Storage Setup”

The complexities of Apple’s Photos.app

Since I have recently written about and recommended multiple Extensions for Apple’s Photos.app, I thought I would share a link to this article by the author of the RAW Power application on what happens “under the covers” when using an Extension. It also covers the difference between an Extension and the “Edit With..” functionality. What is happening is far more complex than you might imagine and will probably explain various inconsistent behaviours you may have observed.

Software Review: On1 Photo RAW 2018

On1 Photo is one of the many editing applications I use to process my photographs. I have previously written about my journey from using a single application (Apple’s Aperture) to many so an update post about the latest version seemed overdue. [Due to a delay in publishing this article, RAW 2019 is now available and 2018 is no longer the latest version!]

The upgrade from On1 Photo 10 to On1 Photo RAW had been a bit bumpy. The new features were great but some older ones had not made the transition. While I did not directly experience too many bugs, there were frequent bug-fix releases with the consequence that it seemed like every time the program was opened it wanted to update itself, interrupting my photo editing session. Consequently I did not rush to upgrade to the 2018 version when it was announced, the new features were not initially compelling and the current version was working well enough.

A few months ago I received a significant discount offer to upgrade. (This was before On1 had announced the 2019 version.) I also noticed that their most recent point release (free upgrade within the 2018 version) had added the ability to manage RAW+JPEG pairs in Browse.  Since this is how I shoot, I had found managing the sets of files separately to be tedious and been looking for a better file management solution.  I was also looking forward to trying out the panorama feature since I capture them too infrequently to invest in dedicated panorama software.

Immediately after starting with Photo RAW 2018 I realised that this was a more significant upgrade than I had expected. The interface felt comfortably familiar but also subtly tweaked to be more streamlined to use. The performance was significantly better too—I could not help feeling that this was how Photo RAW should have been at release, and had now arrived after 18 months of feedback and iterative improvements. 

If you were disappointed with the initial release of On1 Photo RAW then I can thoroughly recommend the upgrade to the 2018 version if you have not settled on some other tool instead. I have not upgraded further to the 2019 version, for similar reasons to why I did not upgrade to 2018 at the beginning. I am also waiting for Luminar 3 to be released since its promised libraries feature is very similar to the browse functionality that I use extensively in On1 and it will be interesting to compare them before committing my money. If you have yet to try On1 Photo RAW then their extensive collection of video tutorials is the best starting point—they can really help you understand how to get pleasing results from it.

RAW Power for MacOS

One of the power features lacking in Apple’s Photos application is the ability to tweak the built-in conversion from RAW to JPEG. The now-discontinued Aperture application allowed manual control of these RAW conversion settings giving the photographer the ability work with more of the captured data to unlock hidden detail without needing a separate specialist application.

RAW Power is a Photos extension that enables this fine-tuning from within Photos. I learned from a YouTube interview with the Developer that he is the former dev lead for Aperture, having left Apple over a year ago, which suggests to me that Apple will likely cede advanced editing functionality to third party developers as I previously speculated.

As a tool with a very specific purpose, its focus makes it simple and effective to use. The interface is clearly laid out and performance nimble, and if it becomes apparent that RAW modifications are not able to improve the photo then you can cancel your edits and return to Photos with one-click.

RAW Power currently costs £9.99, and although this is labelled as promotional pricing, it is my opinion this represents very good value.

iPhone migration: restore from backup or setup from scratch?

In moving to my fifth iPhone I decided it was time to try a fresh install instead of transferring state from my previous one. Apple’s transfer process has always worked works seamlessly but that Star Trek-like transportation of your old phone to the new makes the new one seem, well a little less new somehow. Previously I would have feared losing something small but vital by not using the transfer process but with so much now synchronised between devices by iCloud, it seemed that the most painful and important items were covered. My willingness to experiment was also mitigated by the knowledge that if it all went wrong I could still re-install the new phone from my old backup.

Without the need to wait for a gigabyte of data to be transferred to the new phone, I was up and running very quickly and enjoyed seeing what differences there are between an out-of-the box configuration and my own. With the exception of turning off the sound and vibration notifications for new email, I have customised very little to start with: I want to see if there are any settings or features I have previously overlooked because of some decision I made 7 years ago. Working through my list of apps and choosing to only reinstall those I know I have used recently was also enlightening—there were applications I had forgotten existed buried in never-opened folders, and including some that now crash on startup. I noticed others that are no longer being updated but the developers have instead issued a whole new app instead. I learned that the telltale sign for this is when you tap on the application in your “purchased” list and it fails to display anything about it.

Having chosen which apps would survive the migration and downloaded them all, the main pain point was having to re-authenticate in all of them. The reduced number of apps kept this manageable and I would guess about 50% enabled the use of iCloud Keychain which made it a two-tap process. Given the tedious and error prone nature of typing in a complex password onto a phone keyboard I am shocked that the other 50% do not enable this. Those apps which forced me to lookup and retype my password are certainly strong candidates for deletion if there is an alternative. 1

By not restoring from backup, any applications that store state locally and not in the cloud would lose their data. I was a little worried about my Angry Birds progress but then realised I had not played the game in a very long time anyway, and so far I have discovered only one application which stores data I would like to keep. It is a free app and its paid for version supports data export, which seems fair enough. WhatsApp messages were restored from its own iCloud backup (which it performs nightly) but I did lose my SMS and iMessage history (going back to 2008). Recent iMessages are on my mac anyway and after reviewing the older messages they were all very temporally contextual—“I am here / outside, where are you?”—type stuff. It is noticeable how much longer messages have become recently, perhaps an inevitable consequence of removing the 160 character limit of SMS.

In conclusion, unless you have apps or games that depend on local data, setting up from scratch was not at all painful and it felt really good to have a spring clean. Deleting something always requires metal energy to assess its value, or downside of its loss, and with storage so cheap it is rarely worth the effort. Consequently we accumulate bits and bytes rather too easily, and sometimes a platform migration is a good moment to assess what is no longer required, and start afresh.

  1. Anecdotally, many of those which failed to implement keychain were companion apps from established non-digital companies, for example, airlines and hotel chains. Developers competing for users on the strength of their app alone were far more likely to have implemented it.[]

Too Busy To… available on Apple News

Subscribing to a blog via RSS remains a niche and decidedly geeky activity. Having said that, Apple devices now come with a built-in News.app which, for all the usual Apple gloss, does use RSS. To view this blog in Apple News, visit this link on your iPhone or iPad and tap the + sign in the top right hand corner to subscribe.

If you do not use News.app, Safari’s shared links feature (the @ tab in the bookmarks pane) also allows you to subscribe to this and many other blogs.

A macOS Photo Editing Workflow

This is part of a series of posts describing my move from Apple’s Aperture to Photos.app for managing and editing digital photographs. Previous entries include a feature comparison, third party applications and extensions.

Although Aperture has not received a significant update in three years, I did not feel it was deficient in any way. Having now used a number of recently released other applications 1 in the last few months I have now become aware that Aperture does lag behind the state of the art and it is time to update my toolbox. Another consequence of using different tools is that I now recognise that Aperture is in fact three products in one: RAW converter, photo manager and editor. Given the convenience and advantages of using Apple’s built-in image management, including the iCloud library for device synchronisation, it seems obvious that Apple’s Photos.app should be the starting point for a replacement solution.

When editing, for many photographs I found I could produce the same or better results in Photos.app compared to Aperture, unless I needed to tweak the RAW conversion. Photos’ superior plugin implementation also means that when it cannot get the job done alone it only takes one click to call out to another application. Consequently while Aperture has more built-in tools than Photos.app, the high quality of external applications means that Photos.app plus plugins can get better overall results with no loss of efficiency.

Photos.app handles RAW files but offers no editing abilities above and beyond what is offered for JPEGs. Given the additional time and bandwidth required to upload them to iCloud, along with the greater space consumption on iCloud storage, there seems to be no benefit to offset those costs and I have decided not to store RAW files in Photos.app. Storing my RAW files in a standard folder hierarchy without the obfuscation of a management application also makes it very easy to move these files between tools 2 and platforms in the future.

I have been using Nikon’s Capture NX-D software to convert the RAW files into JPEGs. This is free from Nikon and produces lovely JPEGs which match what is shown on the camera screen, but I found too slow and too difficult to use to make even the most basic edits. I tried a 30 day demo of DxO Optics Pro 10 which produced reasonable JPEGs and was very good at improving certain aspects of a photo (noise removal and some lighting scenarios) but for the average photo is no improvement on the built-in Apple RAW conversion, and not as aesthetically pleasing as Capture NX-D.

In light of these findings, on recent shoots when SD card space has not been an issue, I have set my camera to store RAW+JPEG rather than RAW-only. I have then imported the camera JPEGs directly into Photos.app and reserved RAW edits for only those where the in-camera JPEG is not good enough. In that situation I do then import the RAW into Photos.app and use the excellent DxO Optics Pro for Photos plugin if I think that will solve the problem, or resign myself to fiddle with Capture NX-D if necessary. 3

  1. Nikon’s Capture NX-D, On1 Photo 10, Polarr and DxO Optics Pro.[]
  2. Such as the recently announced On1 Photo RAW.[]
  3. I have on occasion also loaded the RAW into Aperture to compare the results with the other two, and in four out of five cases found Aperture could not do a better job.[]

Pixelmator Retouch Extension

Previously I noted that moving from Aperture to Photos.app meant giving up the ability to selectively apply enhancements using a brush. I speculated this advanced functionality would be something third parties could provide via the extensions API, and the latest version of the superb Pixelmator provides all the brushes I remember having actually used in Aperture: burning, dodging, colour and sharpening. The retouch extension also provides access to Pixelmator’s very impressive repair tool for removing unwanted objects, a serious upgrade to the built-in retouch function.

Also worthy of mention is the Mac version of the Polarr Photo Editor. A slick and efficient editor in its own right, it makes the popular curves adjustment easy to apply without leaving Photos and its de-haze slider is also useful for increasing the clarity of hazy or misty photos.

Photo Editing Apps for Mac

As a follow up to my previous post, I have been evaluating some of the many photo editing apps available for Mac to see how they might fit into my post-Aperture workflow.

For the problem of comparing sets of images the best tool I have found so far is MacPhun’s Snap Select. Although it can only display two photos side by side and not the 8 that Aperture can display simultaneously, I have found it to be effective at picking a single “best shot” from a selection of similar ones, which is my usual use case.

The majority of other apps appear to be focussed on editing and not managing a collection. On1 Photo 10 has a ‘browse mode’ which supports star ratings but it lacks side-by-side viewing and can only display thumbnails—the main focus of the suite is editing. It includes an easy to use portrait editing as well as a versatile effects module with a flexible masking option to apply effects to only parts of an image. I originally came across them because they offered a free set of presets for Aperture which I have used quite a bit. Having purchased this app on the Mac App Store—where it is currently much cheaper than direct from their website, and apparently the same full version although this version does not integrate with applications other than Photos.app. I also found the Resize module to be very useful in making a high resolution 30×20″ print from an older photo I only had as a 16:9-ratio jpeg. I had always thought that up-scaling an image in this way was bound to lead to poor quality but it turns out there are clever algorithms that can be applied to maintain quality. Resize also supports generating an extra border for the image which is then “wrapped” around the edges of a canvas. Without this “gallery wrap” feature, an image can lose a substantial section from the edges when the canvas is 3-4cm thick.

The power of On1’s Effects can be seen in this video. I have yet to really explore this module but initial experiments showed that while using smart layers brings some file format compatibility with photoshop, the resulting files are around 200MB each. This is not relevant if the module is used as a plugin to Photos.app because Photos does not allow edits to be modified further once the plugin has exited, but for advanced work a more compact file format is needed to avoid making the user decide whether they want to ever revisit a set of edits again in future.

My favourite Photos extension so far is definitely DxO Optics Pro. It only offers a small number of enhancements, including noise and haze reduction, but the noise reduction is excellent and worth the money alone. It works best with RAW files, but I have achieved some pleasing results even with camera phone photographs. Highly recommended, and on the strength of the extension I will be trialling their full DxO Optics Pro software when I next have a good batch of shots to process.

Aperture v Photos.app, El Capitan Edition

I have been a very happy user of Apple’s Aperture since 2011. I remember spending a few months using trial versions of both Lightroom and Aperture, before deciding Aperture suited me a little bit better—I think its integrated editing tools were slightly more powerful at the time and it seemed likely that Adobe would be keen not to make the built-in tools so powerful as to compete with their premier product. I was not overly worried when Apple first announced that Aperture would be discontinued because they have a track record of introducing revolutionary new products without every advanced feature in the initial version but then iterating consistently year-on-year until the gap is closed. With that in mind there was much anticipation around this Autumn’s release of OS X El Capitan, and consequently considerable disappointment that support for external editing extensions was the only addition. However it is important to remember that Photos.app was only released six months prior to El Capitan and so this was not a full year of iteration.

Although I had dismissed the initial version of Photos, with the availability of external editors to replace any missing editing tools, perhaps it is time to start thinking about the transition. Photos already has a few features in its favour, for instance it feels faster at navigating between photos, and does not spin for 30 seconds whenever it encounters a video. The advanced tools are comprehensive once you drill down enough to find them, and kudos to Apple for building a textbook example of how to make an interface that provides such a progressive user learning experience. In a taste of what new functionality is being denied Aperture hold outs, the noise reduction in Photos appears much improved over the equivalent in Aperture.

Perhaps the most significant omission is that there is no mechanism to apply an edit to only part of a photo, an equivalent of Aperture’s brushes. This may be a gap that Apple expects editing extensions to fill although I find Apertures’s non-destructive edits much quicker and simpler to use than the layer-mask approach of Photoshop and Pixelmator. There is also no way to display hot/cold regions to see under- and over-exposed areas. Photos.app also has greatly simplified camera-data and EXIF display. These are useful when trying to improve one’s photography “post-mortem” by looking at how the camera was setup for a particular (usually unsuccessful) photograph so their removal is disappointing.

Star ratings are also no longer available. In Aperture each photograph could be assigned a colour and a flag as well as a star rating, so it is easy to see that there were probably too many options for the majority of users who will be much happier with a simple “favourite” function. But when dealing with a large library having different ways to annotate a photograph is useful, a flag can signify a photograph that needs more attention before it is “finished” while star ratings can be used when dealing with many similar photographs of a single subject to distinguish the great from the merely good, and then the 1-star, “bad but captures some unique moment so worth keeping.” Another problem when dealing with multiple exposures of the same subject is that inability to do a side-by-side comparison of two-or-more photos. In Aperture it is possible to bring up all the photographs of a particular subject in a single view and eliminate them one-by-one. This seems to be completely impossible in Photos.app and therefore a complete showstopper for me because I use this feature a great deal when deciding which images from a set to discard and which to publish here.

Which of these missing features Apple will eventually bring to Photos.app is difficult to guess. Star ratings seem the most unlikely to return since only obsessive-compulsive types rate their possessions on a five-point scale, plus Apple already expended the effort to convert the ratings to keywords/tags. I sincerely hope side-by-side comparison returns since that is the raison d’être of both photograph management software and large screens. Brushes require a significantly more complex user interface, especially on an iOS, but are also an ideal use case for Apple’s new iPad Pro Pencil. Or Apple may decide that such advanced editing functionality has no place in a management app, and cede the space to third party developers via the extensions API.

OS X Notes.app and IMAP Accounts

On a fresh install of OS X Yosemite, the notes.app was unable to see the notes stored on my IMAP server. The account was working properly in Mail, and notes.app worked fine with other accounts.

I recall having this same problem with a previous version of OS X, and that it was related to the “IMAP Path Prefix” advanced setting within the Internet Accounts system preference panel. The prefix is set correctly so I was about to give up on this as being an annoying–but–ignorable bug when the very last post in this forum discussion indicated that a cargo-cultish approach of changing the prefix, opening and closing notes, then reverting the setting had fixed it. I can confirm that this solution also worked for me. I kept Mail.app closed for the duration to prevent it being confused, and observed that simply unsetting the value is insufficient, it must temporarily be set to another value, such as “none”, to work.

OS X Terminal.app, bash and UK Keyboards

On an Apple UK keyboard, the # symbol is accessed by pressing ⌥-3 (pronounced option 3). Unfortunately the terminal application is only useable when option has been mapped to the UNIX meta-key, which takes precedence over “special” characters such as #. Thanks to this tumblr post, it is possible to work around this problem:

$ cat .inputrc
"\e3": "#"

Unfortunately .inputrc is a bash-specific configuration file and this does not solve the problem for terminal-based applications.