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Okay, here's some really great news.

  1. iCatcher plays .m4b files without issue. So that's good news right there. Just tried it, works a treat.
  2. You don't need to use a cloud service to import media to it!

    This is thanks to your use of an iMac. AirDrop is your friend. It transfers entirely over your local LAN, very likely at much higher speeds than over your Internet connection. Et voilà:
    1. On your Mac, select the .m4b file.
    2. Command-click. Select the Share menu. In the Share menu, select AirDrop.
    3. In the AirDrop dialog that comes up, point to your iPhone. You may need to unlock your phone.
    4. When the file is finished transferring, you iPhone will ask what app to open it in! Select iCatcher.
    5. iCatcher will ask you what "podcast" (folder) to add it to. You can choose an existing podcast or create a new one.
    6. Done. Now proceed in iCatcher to transfer the file to the Watch.
So slick.

UPDATE: Yes, the .m4b file also plays on the Watch. The one I tried is 714 minutes long! It took a while to transfer from iPhone to Watch, but I just went about my business with the Watch on my wrist and the phone in my pocket, and poof, there it was.

I'm so happy with iCatcher that I've deleted Overcast, Castro and Downcast, none of which do all that I want, while iCatcher does ...with the exception, at this moment, of automatic transfer of desired podcasts to the Watch when new episodes are downloaded. (Soon.)

So once again to add a reality check, if you try the above but with a FOLDER of files, you will not get this happy effect. You can in fact find a place to store the folder that appears to be the iCatcher home folder (and is the same place that stores files/folders dragged into iCatcher via iTunes' File Sharing Window). But in both cases iCatcher appears to be oblivious that files can be added to its storage in this way.

So, like I said: IF your audiobooks consist of a single long file, iCatcher may be great. But if for whatever reason your audiobooks consist of lots of small files, 😢
 
So once again to add a reality check, if you try the above but with a FOLDER of files, you will not get this happy effect... So, like I said: IF your audiobooks consist of a single long file, iCatcher may be great. But if for whatever reason your audiobooks consist of lots of small files, 😢


Hm, haven't tried sending a folder across. But I've selected multiple files at once in Finder (using the usual command-click) and that works.

I'd imagine WatchOS does not yet support folder structures for files or even understand them very well. iOS doesn't either-- try putting a folder of apps inside another folder of apps. Last time I tried this, it did not work.

The technology (and this app) is advancing so rapidly, that might change at some point.
 
Can anyone trying OS7 please confirm whether or not m4b DRM free audiobooks can be sideloaded? Sometimes multiple m4bs make up one book, 48+ hours! I haven’t used my watch for months but may give it another go if this omission has been rectified.
 
Hm, haven't tried sending a folder across. But I've selected multiple files at once in Finder (using the usual command-click) and that works.

I'd imagine WatchOS does not yet support folder structures for files or even understand them very well. iOS doesn't either-- try putting a folder of apps inside another folder of apps. Last time I tried this, it did not work.

The technology (and this app) is advancing so rapidly, that might change at some point.

It's unclear how much of this is Apple's fault and how much is developer not-giving-a-fsck.

(a) You ABSOLUTELY can drag folders to iOS apps in iTunes. Try it. You seem to be confusing a UI choice (don't present the user with folders in Springboard) with a file system functionality (nested folders in APFS). iOS has had nested folders from the beginning. An app like GoodReader makes aggressive use of them.

(b) An app that cared could easily work around this. Even if iOS to WatchOS only allows the transfer of one file at a time, that's an API issue, not a UI issue. The app can still provide a "select all" button and then do its own looping for the transfer. Or it can zip all the files into a single archive (maybe use weakest compression level), then unzip on the watch side. The basic problem is that every app that claims to be doing this just DOES NOT CARE. They are podcast apps, they think podcasts are the only things that matter, and they have added side-loading as a checkbox feature to get suckers (like me) to give them some dollars. They don't give a damn for how well the feature works, just that they can mark it as present.

Castro, Mixtape, iCatcher, Overcast --- all of them DO NOT CARE ABOUT THIS FEATURE. And when the app doesn't care about a feature it's garbage, as we see in all four cases.
 
It's unclear how much of this is Apple's fault and how much is developer not-giving-a-fsck.

...Figured out how to import a full folder of audiobook files into iCatcher.

Turns out it's easy once you know the steps. Maybe not as easy as dragging a folder from A to B, but pretty simple.
  1. Enter the "folder" (podcast) you want to store this set of imports. In my example below, I select the "Imported Media" folder but it can be anything you want.
  2. Click the iCatcher icon near upper right corner
  3. Select the Files App (there are other options too)
  4. Navigate to the folder that contains the DRM-free audiobook files you want to import
  5. Select the ones you want, or Select All
  6. Click "Open".
  7. iCatcher will switch back to your folder and the files will be imported.
(If you have the folder set to auto-transfer new content to your Apple Watch, that will proceed automatically too.)

Video demo below. By the way, if you want a feature, by all means tell the developer. He/she may well give a fsck. Or maybe not: I got no joy from doing that with Castro and Overcast, but the guy behind iCatcher has been super responsive and has implemented several things I've asked for. Ditto with the Forecast Bar, WeatherGraph and Battery Grapher guys. It's a big reason why I'm so happy to recommend their products.

 
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Can anyone trying OS7 please confirm whether or not m4b DRM free audiobooks can be sideloaded? Sometimes multiple m4bs make up one book, 48+ hours! I haven’t used my watch for months but may give it another go if this omission has been rectified.

WatchOS 7 hits the streets tomorrow... I'll try it but fully expect this to work well. Check back then!

UPDATE: Works as I’ve documented here. Improvements are coming too.
 
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...Figured out how to import a full folder of audiobook files into iCatcher.

Turns out it's easy once you know the steps. Maybe not as easy as dragging a folder from A to B, but pretty simple.
  1. Enter the "folder" (podcast) you want to store this set of imports. In my example below, I select the "Imported Media" folder but it can be anything you want.
  2. Click the iCatcher icon near upper right corner
  3. Select the Files App (there are other options too)
  4. Navigate to the folder that contains the DRM-free audiobook files you want to import
  5. Select the ones you want, or Select All
  6. Click "Open".
  7. iCatcher will switch back to your folder and the files will be imported.
(If you have the folder set to auto-transfer new content to your Apple Watch, that will proceed automatically too.)

Video demo below. By the way, if you want a feature, by all means tell the developer. He/she may well give a fsck. Or maybe not: I got no joy from doing that with Castro and Overcast, but the guy behind iCatcher has been super responsive and has implemented several things I've asked for. Ditto with the Forecast Bar, WeatherGraph and Battery Grapher guys. It's a big reason why I'm so happy to recommend their products.

I appreciate that you are trying to be helpful, but you're also not listening!

The problem is not getting the books into the iPhone. That's a mess, but it's doable.
The problem is getting 288 small files from the iPhone TO THE WATCH. THAT is the part where every app demands that you select every file, one at a time, and transfer it one at a time. (Note that EVERY ONE of the bulk file transfers that you have suggested TO THE WATCH have been Apple UI, not developer UI...)

THAT is the UI that makes it clear to me that the developers have (not one of them) ever actually cared about using this feature enough to realize that this sort of 288 rounds of tap, wait, tap, wait is UTTERLY unacceptable.

As for the iCatcher developer, maybe HE is the exception. But I have gone through this already with Mixtape, Overcast, and Castro a year ago, and those apps are still what they are today. That's one reason I am so angry about this -- they know they are shipping garbage, they've been told exactly how it is garbage, and they just DO NOT CARE.

So, yeah, not much interested in banging my head against a wall again. When a feature is CLEARLY broken, not some subtle small edge case, that tells me all I need to know about developer priorities vs checkbox features.



View attachment 953434
 
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I appreciate that you are trying to be helpful, but you're also not listening!

The problem is not getting the books into the iPhone. That's a mess, but it's doable.
The problem is getting 288 small files from the iPhone TO THE WATCH.


Try this:

With your audiobook files in a folder ("podcast") in iCatcher on your iPhone,

  1. Create a new playlist
  2. Add the podcast to this new playlist
  3. In the playlist, select all (using the [...] button near the top right
  4. Click the same button a second time, and select Transfer to Apple Watch.

There may be an even niftier way that I'm still researching, but this works easily and well.
 
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Try this:

With your audiobook files in a folder ("podcast") in iCatcher on your iPhone,

  1. Create a new playlist
  2. Add the podcast to this new playlist
  3. In the playlist, select all (using the [...] button near the top right
  4. Click the same button a second time, and select Transfer to Apple Watch.

There may be an even niftier way that I'm still researching, but this works easily and well.

It never freaking ends! OK, so I jumped through all the hoops so far, and final end product is
- marked all the files in iCatcher
- told them to transfer to to the watch
- a few files start being transferred. Looks good.
- two hours later iCatcher is showing the entire list as "clear" with no red "queued" next to any file. Great
- go to the watch
- 18(!) files have been transferred. Then iCatcher for whatever reason decided to call it a day.
And those files transferred are in random order with no apparent way to sort them out on the watch.

[[begin rant]]

Don't you feel that this is utterly INSANE!
I have to preprocess the files to get the ordering correct (because iCatcher does lexical ordering not semantic ordering, so files number 10-1 xxx come before 2-1 xxx.
Jump through hoops to get the files into iCatcher.
(ONE book at a time because otherwise everything is mixed up in _Imported Media_)...
Then get it into a playlist.
Then clean out _Imported Media_
Then transfer the playlist to the watch. Via what appears to be multiple copy attempts.
To land up with randomly ordered files on the watch. So much for my attempting to get the numbering correct in step 1...

All within a context that insists that what I am really doing is manipulating podcasts and insists on using podcast terminology for everything.

I am impressed that you finally figured out a way to achieve this. I am throughly unimpressed that such a Rube Goldberg set of steps is necessary. There was a time in my life where I treated this sort of thing as a challenge, something that I could and would solve, no matter how long it took. I'm too old for that now: if your app claims to do X, I expect it to do X with a maximum of three user interactions!

All I want is a damn watchos AUDIOBOOK app, not these insanely complex podcast players that have to be treated like diva's to coax them to do what should be basic and trivial tasks.
You don't deserve this rant, it's not your personal fault. But goddammit, 50 million apps on the app store, and not one of them is interested in actually doing this task well rather than being yet another damn podcast app? WTF???
 
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All I want is a damn watchos AUDIOBOOK app, not these insanely complex podcast players that have to be treated like diva's to coax them to do what should be basic and trivial tasks.

I’ll second this, as long as it works with side loaded m4bs, as I’ve told Apple many times over the past year.
 
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Hm, haven't tried sending a folder across. But I've selected multiple files at once in Finder (using the usual command-click) and that works.

I'd imagine WatchOS does not yet support folder structures for files or even understand them very well. iOS doesn't either-- try putting a folder of apps inside another folder of apps. Last time I tried this, it did not work.

The technology (and this app) is advancing so rapidly, that might change at some point.

Hey sjinsjca! So after reading all you very enthusiastic and detailed reviews and replies on the iCatcher! app I've decided to buy it, but I'm having trouble loading the files onto the apple watch. They get stuck in the "queued" section forever, the little loading wheel doesn't move, and I've tried everything I can think of. Do you have any suggestions on what I should do and how long each transfer should take? It's an audiobook where each file is about 20Mbs, 40 mins of audio.
I'd really appreciate any help here, as this is one of the main reasons why I bought the watch. Thanks!
 
Hey sjinsjca! So after reading all you very enthusiastic and detailed reviews and replies on the iCatcher! app I've decided to buy it, but I'm having trouble loading the files onto the apple watch. They get stuck in the "queued" section forever, the little loading wheel doesn't move, and I've tried everything I can think of. Do you have any suggestions on what I should do and how long each transfer should take? It's an audiobook where each file is about 20Mbs, 40 mins of audio.
I'd really appreciate any help here, as this is one of the main reasons why I bought the watch. Thanks!

Dang, sorry to hear you're having frustrations. I've had this happen maybe twice in my months of intensive iCatcher usage; rebooting the Watch laxated the process. Try that.

You might need to delete and re-start the frozen downloads after rebooting the Watch.
 
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Hi guys, any updates on this? or new apps?
I too have been searching relentlessly.
I would like to listen to audiobooks whilst partaking in tediously dull activities such as swimming or running.

Does iCatcher remember where you stopped and can resume when needed?
Or do you need to *remember* then fast forward to that point when you wish to resume your audio book the next day?

And no 15 second rewind / FForward buttons yet?

update: bought it. It does have the 15sec buttons.
It’s taken 10mins to transfer half of a 200mb file. Still waiting.

tip: I have the FileBrowser app. It enables me to navigate networks and my networked computers, to access and edit, copy, delete folders and files. I’m new to the files app (a toddler version of finder or windows explorer?) but found that FileBrowser has been integrated into the Files app. ICatcher seems to use this Files app (and thus FileBrowser) as its navigation tool.

hope that makes sense, and hope they rename the files app so it is easier to explain these things.

The Apple Watch is really overpriced when you consider how limited it is - even when the tech is already there.
 
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Hi guys, any updates on this? or new apps?
I too have been searching relentlessly.
I would like to listen to audiobooks whilst partaking in tediously dull activities such as swimming or running.

Does iCatcher remember where you stopped and can resume when needed?
Or do you need to *remember* then fast forward to that point when you wish to resume your audio book the next day?

And no 15 second rewind / FForward buttons yet?

update: bought it. It does have the 15sec buttons.
It’s taken 10mins to transfer half of a 200mb file. Still waiting.

tip: I have the FileBrowser app. It enables me to navigate networks and my networked computers, to access and edit, copy, delete folders and files. I’m new to the files app (a toddler version of finder or windows explorer?) but found that FileBrowser has been integrated into the Files app. ICatcher seems to use this Files app (and thus FileBrowser) as its navigation tool.

hope that makes sense, and hope they rename the files app so it is easier to explain these things.

The Apple Watch is really overpriced when you consider how limited it is - even when the tech is already there.
How about the remembering to play from where it was left functionality?
Also in terms of transfer speed? is it always slow?
 
Hi guys, any updates on this? or new apps?
I too have been searching relentlessly.
I would like to listen to audiobooks whilst partaking in tediously dull activities such as swimming or running.

Does iCatcher remember where you stopped and can resume when needed?
Or do you need to *remember* then fast forward to that point when you wish to resume your audio book the next day?

And no 15 second rewind / FForward buttons yet?

update: bought it. It does have the 15sec buttons.
It’s taken 10mins to transfer half of a 200mb file. Still waiting.

tip: I have the FileBrowser app. It enables me to navigate networks and my networked computers, to access and edit, copy, delete folders and files. I’m new to the files app (a toddler version of finder or windows explorer?) but found that FileBrowser has been integrated into the Files app. ICatcher seems to use this Files app (and thus FileBrowser) as its navigation tool.

hope that makes sense, and hope they rename the files app so it is easier to explain these things.

The Apple Watch is really overpriced when you consider how limited it is - even when the tech is already there.
I have begged Stratospherix to build a native watch app of FileBrowser.

I would love it, as one it would add so much functionality to the watch - play music (without using iTunes / music), play podcasts, view videos, view documents etc.

Secondly, imagine being away, losing you iPhone or it going wrong or stolen, and being able to download all your important files locally, from the watch to a replacement iPhone.
 
I joined the forums to +1 and thank op for this thread.

Will tip icatcher once I'm sure it's working for my needs properly.

I think that some of the complaints about icatcher are misguided. So far; it's the easiest / most reliable way I've found to sideload mp3 onto the apple watch.

The vitriole and discontent should be directed at APPLE. How can apple watch integration be so worthless. It's horrible. Settings and configuration is randomly found everywhere. It's like a wild goose chase => is it on the phone? on the watch? in the app? in the settings?


And the lack of reliable podcast syncing is plain unacceptable. This does not feel like a "walled garden" apple product. More like something that was cobbled together by a couple of grad students.

I'm sure apple has a reason for this. But lack of resources is not one of them.

Anyways, thanks for providing the only reliable mp3 transfer method i've found yet!
 
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what i do >
I use outcast, podcast player for apple watch
upload my audiobook to spotify podcast, copy link, and paste to watch, app downloads it from the net
 
Unfortunately, iCatcher discards chapters in AudioBooks. Then that makes it useless for people who want to transfer .m4b AudioBooks to the AppleWatch.
 
Bookplayer, my favorite iOS audiobook app, is adding standalone Watch playback. The dev posted a couple of weeks ago that work is ongoing, so hopefully soon. It is free and open source, there is a subscription for I believe iCloud sync which should sync progress across devices (would be great if Watch app has this too.)

In the meantime, I found another app called WatchAudio that seems to have pretty robust support for standalone audio playback. No RSS workarounds to transfer files, you just open the app on iPhone and Watch at same time and pick files to transfer. For audiobooks, resuming playback location is supported. Chapter support requires $4 premium purchase (I have not tried yet.) The free version is also limited to 15 files, which is fine if you mainly have m4b or complete single audiobook files.
 
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Castro and Overcast both allow sideloading to your Phone but neither seems to support transferring those sideloaded files to the Watch. Syncing seems to be spotty regardless of the app. So, I've been watching this thread, hoping someone has discovered an app that will do this well, while continuing the hunt on my own.

And: success. Read on. (The following includes many updates over several days.)

Executive Summary

iCatcher is an excellent, stable, low-cost and highly functional app for playing non-DRM audio and audiobook files independently and off-network on the Watch, as well as normal podcasts.

How to side load audio files into iCatcher

Method 1:

Use iCatcher's built-in tool from within the Imported Media "podcast" (or any other) to transfer files from iCloud or other Files.app-compatible cloud service:


The steps:
  1. Start with the iCatcher app on your iPhone. In the Settings pane in the iPhone app, select Import Media.
  2. Click Import From... and navigate to your .MP3 audio files. Your files can be in Dropbox, in iCloud, or wherever else might be convenient. UPDATE: iCloud seems more reliable. Best to first open the Files app to ensure that the files you want to import are actually resident on your phone-- if you see a cloud icon for a file in the Files app, click it so it downloads. (Commence the file imports from within iCatcher. I was unable to get the share menu in Dropbox's app or the Files app to convey more than one file at a time to iCatcher. This seems to be an iOS bug.)
  3. Click the Select button. Click on files you want to transfer. Click Open. I have had good luck selecting up to 30-40 files at a time on my iPhone XS. Above 40-some files, the select process can hang. This may be a RAM thing and if so, the maximum number of files you can work with at a time might be different for a different phone model. Again, iCloud has seemed more reliable. If you have piles of files, you can always import in batches. The process is fast.
  4. The files will appear under the "Available for Import" label. Click the All button at the upper right corner. Click the Next button.
  5. Under the "Podcast & Episode Selection" you can either leave this blank (in which case the file will eventually end up in a "Podcast" entitled "Imported Media") or you can enter a name for a new "Podcast" that will contain this and other files. So, this might be a good place to put the audiobook's name.
  6. Finally, click "Save". Now, navigate to the podcasts list.
  7. You'll find the newly imported files in the "podcast" you specified in step 5. In it, swipe right on each file. Click Send to Watch. There will be a small "transferring" label as it sluices across to the Watch. It's a slow process... be patient. Maybe putting it on the charger might speed things up. Unfortunately this step must be performed one at a time for your files. Transferred files seem to take time to show up in iCatcher on the Watch even after the transfer is shown as complete on the iPhone.
Method 2:

Use AirDrop to load your files from a Mac or iDevice to iCatcher on your iPhone, after which you can instruct it to transfer some or all of them to your Watch. See post 19 in this thread.


Syncing to the Watch

iCatcher's watch sync works reliably, but you must currently specify the files to transfer manually. In particular, iCatcher is unable to automagically transfer new files (such as automatically-downloaded daily podcasts) to the Watch. (Soon.)

Really, the only negative regarding iCatcher is that the user interfaces for iCatcher's iPhone and Watch apps are not as slick as Castro's or Overcast's. (But it doesn't suffer the usability and discoverability fails of Castro in particular.) It's serviceable if not stylish. I'll take functionality over fashion any day.

And iCatcher is really superb in what it does, and it does all this without an upcharge or annual fee.

Independent of whatever app you choose, organizing your imported files might take some thought. In my case, I had several dozen files intended to be played in order, but the content creators' file naming system wasn't well designed for ordering the files. So, I renamed the files manually in the iCloud folder on my Mac before importing into iCatcher, adding a couple of characters at the beginning of the filename ("1a", "1b",...) to ensure a simple alphabetic listing would give me what I wanted. Then, after importing, open iCatcher on the Watch and navigate to the "podcast" containing your imported files. Force-press on the file list on the watch, and select "Pod.Title A-Z" as the ordering. (You can also do this in the Settings for iCatcher on the Watch.) The results will have podcast episodes grouped together, by title. So, your imported media will show up together and in the order you want. Frankly, I'd rather see a folder structure like other podcast apps have, and I'd love to see the ability to import a folder of files rather than dealing with them one by one. All things in time.

Summarizing: I've spent significant time (and, in the cases of Castro and Overcast, money) evaluating:
  • Castro, which is gorgeous but mostly undocumented, and (for my podcast-intensive usage) unintuitive and opaque (what's the difference between the queue and inbox?). It doesn't sync to the Watch reliably and it doesn't sync sideloaded files to the Watch at all. Sideloading is part of a paid annual option, requires iCloud, and is slickly implemented.
  • Overcast, also quite nicely designed... but it doesn't sync to the Watch reliably and it doesn't sync sideloaded files to the Watch at all. Sideloading is part of a paid annual option and is based on uploading your files to Overcast's server, so it can be used for files from a PC or something.
  • iCatcher, which ticks all the functionality boxes. It syncs reliably to the Watch. It syncs sideloaded files to the Watch. Files can be sideloaded from any cloud service that works with your iPhone's Files app, though iCloud has so far proven to be the more trouble-free option for me so far. Files can also be sideloaded using AirDrop! See post 19 below.

Summary

iCatcher comes closest to the ideal functionality for a podcast app, especially for those like OP who want to listen to audiobooks and other files and that aren't podcasted. Suggestions for improvement might include:
  • A proper folder structure on the Watch (as in its iPhone app),
  • Automatic syncing to the watch when specified podcasts are updated (Edit: coming!),
  • Clearer navigation on the Watch,
  • Faster, less opaque transfers to the Watch (are you listening, Apple?)
As a bonus, the developer is responsive and eager for feedback. He doesn't charge for all this functionality, and there are no annual in-app purchases or subscription fees. The app does have a tip-jar, and I highly recommend you use it, as this app is a keeper.
DUH… Isn’t it always the way! Now that I’ve posted this I find that Send to Watch is available if I look at teh book in iCatcher in Downloads, not podcasts. I think it may be on the way 🤞

Apologies as I’m sure this will sound stupid, but I can’t get Send to Watch to appear in iCatcher, even though I’m sure I’ve followed all the steps. Thank you and others for all your help with this. I wish I could manage the final step! I have a new Apple Watch 10 and am desperately trying to get some books onto it (other than Audible) so that I can leave iPhone behind when I go out. Please help if possible.
 
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Bookplayer, my favorite iOS audiobook app, is adding standalone Watch playback. The dev posted a couple of weeks ago that work is ongoing, so hopefully soon. It is free and open source, there is a subscription for I believe iCloud sync which should sync progress across devices (would be great if Watch app has this too.)

In the meantime, I found another app called WatchAudio that seems to have pretty robust support for standalone audio playback. No RSS workarounds to transfer files, you just open the app on iPhone and Watch at same time and pick files to transfer. For audiobooks, resuming playback location is supported. Chapter support requires $4 premium purchase (I have not tried yet.) The free version is also limited to 15 files, which is fine if you mainly have m4b or complete single audiobook files.
Trying WatchAudio now, thanks. Hard to believe there might finally be a dedicated app for this! Thanks for mentioning it here 👍

Edit: Wow, it’s working! Naturally it took a while to transfer the book (a zip file, which the app unzipped on the iPhone) but I’ve now turned off the phone and I’m listening to the book on my watch 😱 I’m shocked because I bought my first Apple Watch (SE) two years ago very largely to do this, but at that time it seemed to be impossible. Now, finally, there seems to be a dedicated app and I’ll be able to go out for my walk, shortly, and leave my phone at home :) (Though I suppose I’ll actually pack it in my rucksack, just in case…) Thank you again, @madmaxmedia ❤️
 
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Trying WatchAudio now, thanks. Hard to believe there might finally be a dedicated app for this! Thanks for mentioning it here 👍

Edit: Wow, it’s working! Naturally it took a while to transfer the book (a zip file, which the app unzipped on the iPhone) but I’ve now turned off the phone and I’m listening to the book on my watch 😱 I’m shocked because I bought my first Apple Watch (SE) two years ago very largely to do this, but at that time it seemed to be impossible. Now, finally, there seems to be a dedicated app and I’ll be able to go out for my walk, shortly, and leave my phone at home :) (Though I suppose I’ll actually pack it in my rucksack, just in case…) Thank you again, @madmaxmedia ❤️

I'm really glad it worked out! I ended up paying for the full version, and have been very satisfied with it. iCatcher sounds good too but since it is more for podcasts it lacks chapter support in m4b files, which is a big deal for audiobooks.

One tip for file transfers in WatchAudio (and probably other apps that involve side loading)- Apple Watch will default to using Bluetooth for file transfers to save battery, but it's slow. If you turn off Bluetooth on your iPhone (not in Control Center but in the actual Settings app), the transfer will switch to Wifi and should go a lot faster.

My one minor complaint with WatchAudio is that when I use forward/skip controls on my headphones, it defaults to next/previous chapter with audiobooks rather than say jump forward/rewind 30 seconds. You can forward/rewind with the onscreen display so that's fine, but occasionally I'll accidentally activate the chapter commands with my earphone controls while I'm running. So it would be nice to be able to customize this behavior.

I might try Bookplayer at one point, although I wish it was a one-time fee (the basic free app is fully featured, just no Watch support.) The nice thing about Bookplayer is that I think it should sync playback progress across all devices it is installed on.
 
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It never freaking ends! OK, so I jumped through all the hoops so far, and final end product is
- marked all the files in iCatcher
- told them to transfer to to the watch
- a few files start being transferred. Looks good.
- two hours later iCatcher is showing the entire list as "clear" with no red "queued" next to any file. Great
- go to the watch
- 18(!) files have been transferred. Then iCatcher for whatever reason decided to call it a day.
And those files transferred are in random order with no apparent way to sort them out on the watch.

[[begin rant]]

Don't you feel that this is utterly INSANE!
I have to preprocess the files to get the ordering correct (because iCatcher does lexical ordering not semantic ordering, so files number 10-1 xxx come before 2-1 xxx.
Jump through hoops to get the files into iCatcher.
(ONE book at a time because otherwise everything is mixed up in _Imported Media_)...
Then get it into a playlist.
Then clean out _Imported Media_
Then transfer the playlist to the watch. Via what appears to be multiple copy attempts.
To land up with randomly ordered files on the watch. So much for my attempting to get the numbering correct in step 1...

Check out Bookplayer. I am pretty sure the iOS/iPad apps support books stored as multiple files in folders, so the Watch app may as well. Obviously by the title, it is specifically designed for books.

I generally create m4b files myself but obviously everyone has different preferences. If you wish to give this a try (even if only for books that you listen to on your Watch), check out AudioBookBinder- it is a free app that easily creates m4b files out of multiple book files, and automatically creates chapter marks for the files (I think it is MacOS only.)
 
I'm really glad it worked out! I ended up paying for the full version, and have been very satisfied with it. iCatcher sounds good too but lacks chapter support in m4b files, which is a big deal for audiobooks.

One tip for file transfers in WatchAudio (and probably other apps that involve side loading)- Apple Watch will default to using Bluetooth for file transfers to save battery, but it's slow. If you turn off Bluetooth on your iPhone (not in Control Center but in the actual Settings app), the transfer will switch to Wifi and should go a lot faster.

My one complaint with WatchAudio is that when I use forward/skip controls on my headphones, it defaults to next/previous chapter with audiobooks rather than say jump forward/rewind 30 seconds. You can forward/rewind with the onscreen display so that's fine, but occasionally I'll accidentally activate the chapter commands with my earphone controls while I'm running. So it would be nice to be able to customize this behavior.

I might try Bookplayer at one point, although I wish it was a one-time fee (the basic free app is fully featured, just no Watch support.) The nice thing about Bookplayer is that I think it should sync playback progress across all devices it is installed on.
Thanks for that tip about turning off Bluetooth. Transfers were taking forever! I’ll try one now with no Bluetooth and see what difference it makes. Thanks again for the tip about WatchAudio :)

@madmaxmedia Can you suggest something to turn MP3s into M4b? I noticed above you suggested AudioBookBinder but unfortunately I’m using a PC (as well as an iPhone/iPad) and that’s only for Mac. I’ve tried to search for a good one but I gave up as I couldn’t sort the wheat from the chaff.
 
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