Title: Default attachment folder setting failing to route .tif/.tiff files on Mac
Hi everyone,I am having a frustrating issue with automatic file routing that I have been trying to fix for over two hours.
I am hoping someone here can point out what is going wrong under the hood.
My Setup:OS: macOSVault Name: postcard archiveFolder Structure:01_Family_History02_Postcards (Contains my active note named test card)03_scans (Target folder for all scan attachments)The Problem:I have configured Obsidian to automatically route all new attachments directly into 03_scans. Despite the settings being perfectly applied, the automatic file transfer fails completely when I drag and drop a file into my note.In Settings > Files and links, “Default location for new attachments” is set to “In the folder specified below”.The specified folder path is typed exactly as 03_scans (no leading or trailing slashes).“New link format” is set to “Absolute path in vault”.When I drag a file (e.g., card 56_ back.tif) directly into the note, Obsidian creates the internal link text ![[card 56_ back.tif]], but the text immediately turns red/purple, indicating a broken link.The physical file is not being moved into the vault or the 03_scans folder at all—the folder remains completely empty., and the red link text goes away, so the app clearly recognizes the file and the path once it’s manually placed there.Why is Obsidian failing to execute the physical file transfer to the designated attachment folder upon drag-and-drop, despite the settings being explicitly configured for it? Any insight into macOS permission conflicts or core bugs regarding .tif routing would be greatly appreciated.
Forum Title: Drag-and-drop failing to import/route .tif and .tiff files on macOS
Body:
Hi everyone,
I am having a frustrating issue with automatic file routing on macOS that I’ve been trying to fix for hours. I finally figured out what is happening, but I need some insight into how to fix it or work around it.
My Setup
OS: macOS
Vault Name: postcard archive
Folder Structure:
01_Family_History
02_Postcards (Contains my active note named test card)
03_scans (Target folder for all scan attachments)
The Problem
I configured Obsidian to automatically route all new attachments directly into 03_scans.
Default location for new attachments: “In the folder specified below”
Folder path: typed exactly as 03_scans
New link format: “Absolute path in vault” [1, 2]
When I drag a file (e.g., card 56_ back.tif) directly from Finder into my note, Obsidian creates the link text ![[card 56_ back.tif]], but it immediately turns red/purple, indicating a broken link.
The physical file is not moved into the vault or the 03_scans folder at all; the target directory remains completely empty. However, if I manually drop the .tif file into 03_scans via macOS Finder, Obsidian indexes it immediately and the link works.
Why This Happens
Obsidian does not recognize .tif / .tiff as standard embeddable image formats natively. Because it treats them as unsupported binaries during a drag-and-drop action, it writes the link text but fails to trigger the background file-copy protocol to the designated attachment folder.
Questions for the Community
Is there a core setting or an entry in appearance / files where we can force Obsidian to recognize .tif extensions as standard media attachments?
Are there any community plugins that override the default drag-and-drop file extension whitelist to allow physical routing of .tif archives?
Outside of mass-converting my archive to .png, what is the best workflow to handle high-resolution .tiff scans seamlessly?
Any insight or plugin recommendations would be greatly appreciated!
If you want to keep working while waiting for forum replies, let me know if you want the quick setup steps for Binary File Manager or Local Images Plus plugins to force the copy process to work automatically.
While .tif files aren’t an accepted file format, I think your LLM led you astray with this second part. When dragged into a note (Live preview), the .tif is copied to the correct folder on my end, with the correct link.
source mode (top) | Live preview (bottom)
No.
They are moved to the correct folder on my end (see above).
I’d search the community plugin gallery to see if any enable viewing .tif files within Obsidian.
Also, what’s the location of your vault in the file system? Is it in iCloud Drive? If iCloud Drive isn’t set to keep that vault folder always dowloaded, new notes or attachments dragged in could be offloaded to the cloud. That will produce some odd behavior.
It’s not as much viewing the .tif as I’ve scanned the postcard onto my desktop and dragged it across into the open page on obsidian to store it in the scan folder( 03) - whilst all postcard details get stored in the postcard folder ( 02) and other important information in the family history ( 01 ) folder.
I don’t need to view it in obsidian I just need it to follow its root path and when added sit n 03 scans automatically . I have a very large collection to get into so it needs to work seamlessly
In theory no, but it adds more to watch out for. Is the drive a SSD or spinning disk? What’s the connection speed? USB-2? USB-3? Thunderbolt? Is the connection stable. i.e., is the drive easily disconnected by bumping the cable or anything like that?
I would try running a vault on an internal drive as a test to see the behavior there.
Might be a bit slow with the spinning disk(?), but I would trust that setup.
All my media files and backups are on external spinning disks, but my Obsidian vaults are all internal, so I don’t have experience with using a vault on one.
