%PDF-1.4 %âãÏÓ 1 0 obj << /Type /Catalog /Pages 2 0 R >> endobj 2 0 obj << /Type /Pages /Count 7 /Kids [5 0 R 7 0 R 9 0 R 11 0 R 13 0 R 15 0 R 17 0 R] >> endobj 3 0 obj << /Type /Font /Subtype /Type1 /BaseFont /Helvetica >> endobj 4 0 obj << /Type /Font /Subtype /Type1 /BaseFont /Helvetica-Bold >> endobj 5 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 6 0 R >> endobj 6 0 obj << /Length 4917 >> stream BT /F2 22 Tf 0.06 0.08 0.12 rg 1 0 0 1 46 789.89 Tm (How to Delete a Stuck Outbox Email That Freezes) Tj ET BT /F2 22 Tf 0.06 0.08 0.12 rg 1 0 0 1 46 762.89 Tm (Apple Mail on macOS Tahoe) Tj ET BT /F2 11 Tf 0.72 0.14 0.18 rg 1 0 0 1 46 725.89 Tm (TechRounder PDF Edition) Tj ET BT /F1 9.5 Tf 0.36 0.39 0.46 rg 1 0 0 1 46 709.89 Tm (Live article:) Tj ET BT /F1 9.5 Tf 0.36 0.39 0.46 rg 1 0 0 1 46 697.39 Tm (https://www.techrounder.com/how-to/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe/) Tj ET q 0.82 0.85 0.9 RG 1 w 46 678.89 m 549.28 678.89 l S Q BT /F1 10 Tf 0.24 0.27 0.32 rg 1 0 0 1 46 666.89 Tm (By Vipin PG | Published September 8, 2026 | Updated September 8, 2026 | Format: Guide | 10 min read) Tj ET BT /F2 13 Tf 0.72 0.14 0.18 rg 1 0 0 1 46 643.89 Tm (Quick answer) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 623.89 Tm (A huge attachment can leave Apple Mail in a bad loop on macOS Tahoe. The message sits in Outbox, Mail) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 608.89 Tm (keeps trying to process it, memory usage climbs, and the app freezes before you have enough time to) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 593.89 Tm (delete the message normally.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 568.89 Tm (A huge attachment can leave Apple Mail in a bad loop on macOS Tahoe. The message sits in Outbox, Mail) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 553.89 Tm (keeps trying to process it, memory usage climbs, and the app freezes before you have enough time to) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 538.89 Tm (delete the message normally. Taking the Mac offline may stop the send attempt, but in some cases the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 523.89 Tm (message returns as soon as Mail is reopened.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 501.89 Tm (This happened in a recent macOS Tahoe 26.6.2 case after a roughly 30 GB file was attached to an) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 486.89 Tm (outgoing message. The message never appeared in webmail because it was still stored in Mail's local) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 471.89 Tm (Outbox. The successful fix was to quit Mail and remove the stuck Outbox data under the user's Mail) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 456.89 Tm (library.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 434.89 Tm (On Tahoe, the relevant Mail store is commonly under:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 410.89 Tm (~/Library/Mail/V10/) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 392.39 Tm (The exact Outbox path varies because Mail uses opaque account and mailbox folder names. A typical) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 377.39 Tm (path eventually leads to:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 353.39 Tm (~/Library/Mail/V10/.../Outbox.mbox/.../Data) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 334.89 Tm (The safest way to deal with it is to keep Mail offline, close Mail completely, find the correct Outbox,) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 319.89 Tm (move its data somewhere safe, and only delete that backup after Mail is working again.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 297.89 Tm (Note: `V10` is the name of Mail's on-disk data store used on current macOS versions. It is not the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 282.89 Tm (version number shown for the Mail application itself.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 254.89 Tm (Try the normal Outbox deletion once) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 230.89 Tm (If Mail stays responsive for long enough, try the simple route before touching its files.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 208.89 Tm (1. Disconnect Wi-Fi and Ethernet.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 192.09 Tm (2. Open Mail.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 175.29 Tm (3. Select Outbox under "On My Mac" or the affected account.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 158.49 Tm (4. Select the stuck message and delete it.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 141.69 Tm (5. Quit Mail normally with Command-Q.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 124.89 Tm (6. Reopen Mail while still offline and check whether the message is gone.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 108.09 Tm (If the message comes back, Mail freezes before the deletion finishes, or the app runs out of memory) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 93.09 Tm (again, stop reopening Mail and use the filesystem method below.) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 1 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 7 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 8 0 R >> endobj 8 0 obj << /Length 4597 >> stream BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 789.89 Tm (Before editing the Mail library) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 765.89 Tm (Mail's Library folder contains real mailbox data. A mistake here can affect other mail stored locally,) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 750.89 Tm (especially messages under "On My Mac.") Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 728.89 Tm (Make a Time Machine backup if one is available. Apple states that Time Machine backs up email along) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 713.89 Tm (with other user files. At minimum, keep a copy of the Outbox you are about to change.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 691.89 Tm (With an extremely large attachment, duplicating the whole Outbox may require more free disk space) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 676.89 Tm (than the Mac has. In that situation, moving the problem files to a temporary folder on the same disk is a) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 661.89 Tm (practical alternative. Do not empty the Trash or delete the temporary copy until Mail has opened) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 646.89 Tm (normally and your other mailboxes look correct.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 618.89 Tm (Step 1: Disconnect the Mac from the network) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 594.89 Tm (Turn off Wi-Fi and disconnect Ethernet before opening Mail again.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 572.89 Tm (This prevents Mail from retrying the outgoing message while you work. It also removes the chance) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 557.89 Tm (that a partially processed message suddenly leaves the Mac while you are trying to clean up the queue.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 535.89 Tm (Leave the Mac offline until the stuck message has disappeared from Mail.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 507.89 Tm (Step 2: Quit Mail completely) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 483.89 Tm (If Mail is still responsive, press Command-Q.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 461.89 Tm (If it has frozen, press Option-Command-Esc, select Mail, and choose Force Quit.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 439.89 Tm (Do not change files inside Mail's data store while Mail is actively using them. A normal quit is) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 424.89 Tm (preferable when possible because the app can finish writing its current state. Force Quit is) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 409.89 Tm (appropriate when Mail no longer responds.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 381.89 Tm (Step 3: Open the Tahoe Mail data folder) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 357.89 Tm (In Finder:) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 335.89 Tm (1. Click Go in the menu bar.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 319.09 Tm (2. Choose Go to Folder.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 302.29 Tm (3. Enter:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 283.49 Tm (~/Library/Mail) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 264.99 Tm (1. Open `V10` if it is present.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 248.19 Tm (The V10 directory can contain folders with long UUID-style names rather than recognizable email) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 233.19 Tm (account names. That makes manual browsing confusing, especially when several accounts are) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 218.19 Tm (configured.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 196.19 Tm (Do not delete the V10 folder itself. It contains far more than the stuck Outbox.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 168.19 Tm (An easier way to find every Outbox with Terminal) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 144.19 Tm (Terminal can locate the Outbox folders without requiring you to guess which UUID belongs to which) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 129.19 Tm (account.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 107.19 Tm (Open Terminal and run:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 83.19 Tm (find "$HOME/Library/Mail/V10" -type d -name "Outbox.mbox" -print) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 2 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 9 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 10 0 R >> endobj 10 0 obj << /Length 4753 >> stream BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 789.89 Tm (If you want to avoid assuming the store is V10, use:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 765.89 Tm (find "$HOME/Library/Mail" -type d -name "Outbox.mbox" -print) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 747.39 Tm (You may get more than one result. That is normal when Mail has multiple accounts or local stores.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 725.39 Tm (To compare their sizes, run:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 701.39 Tm (find "$HOME/Library/Mail/V10" -type d -name "Outbox.mbox" -exec du -sh {} \\;) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 682.89 Tm (An Outbox containing a huge attachment should usually stand out by size.) Tj ET BT /F2 13 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 654.89 Tm (If Terminal says "Operation not permitted") Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 632.89 Tm (macOS protects Mail data with its privacy controls. Go to System Settings > Privacy & Security > Full) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 617.89 Tm (Disk Access and allow Terminal access, then quit and reopen Terminal before trying the command) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 602.89 Tm (again.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 580.89 Tm (Apple describes Full Disk Access as permission to access files from other apps, including Mail. There) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 565.89 Tm (is no need to disable System Integrity Protection for this task.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 537.89 Tm (Step 4: Back up or quarantine the affected Outbox) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 513.89 Tm (Once you have found the suspicious `Outbox.mbox`, open it in Finder. The internal structure can) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 498.89 Tm (contain one or more additional opaque folders before you reach `Data`.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 476.89 Tm (The Tahoe case that prompted this guide was fixed by clearing the contents under the affected) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 461.89 Tm (`Outbox.mbox/Data` area.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 439.89 Tm (Before doing that, preserve what is there.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 417.89 Tm (If disk space allows, copy the affected `Outbox.mbox` to an external drive or another safe location.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 395.89 Tm (If copying tens of gigabytes is impractical, create a temporary folder such as `Mail Outbox Backup`) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 380.89 Tm (on the Desktop and move the contents of the affected `Data` directory into it while Mail is closed. A) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 365.89 Tm (move on the same disk normally avoids creating another full copy of the huge attachment.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 343.89 Tm (This also gives you a way back if you discover that another unsent message was stored in the same) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 328.89 Tm (Outbox.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 300.89 Tm (Step 5: Remove the stuck Outbox data) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 276.89 Tm (With Mail closed and the Mac still offline, clear the contents of the `Data` directory inside the affected) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 261.89 Tm (`Outbox.mbox`.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 239.89 Tm (Do not remove neighboring account folders, `MailData`, Inbox mailboxes, Sent mailboxes, or the entire) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 224.89 Tm (V10 folder.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 202.89 Tm (Clearing the whole Outbox data area can remove other unsent messages queued in that same local) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 187.89 Tm (Outbox. If there are messages you need to keep, preserve the Outbox first and avoid permanently) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 172.89 Tm (deleting the backup until you have checked it.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 150.89 Tm (For the reported Tahoe 26.6.2 problem, clearing the affected Outbox data removed the oversized) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 135.89 Tm (message and allowed Mail to open normally again.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 107.89 Tm (Can you delete only the giant message instead?) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 3 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 11 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 12 0 R >> endobj 12 0 obj << /Length 5057 >> stream BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 789.89 Tm (Sometimes, but it is harder to give a safe universal file path for one message because Mail's internal) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 774.89 Tm (layout can split message data and attachments across nested folders.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 752.89 Tm (Advanced users can inspect the affected Outbox and look for abnormally large or recently modified) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 737.89 Tm (files. This command lists the largest files near the end of the output:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 713.89 Tm (find "/full/path/to/Outbox.mbox" -type f -exec du -h {} \\; | sort -h | tail -20) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 695.39 Tm (Replace `/full/path/to/Outbox.mbox` with the path you found earlier.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 673.39 Tm (If one file clearly accounts for most of the Outbox size, moving that file to a temporary folder may be) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 658.39 Tm (enough. The association between a message record and its attachment files is not always obvious, so) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 643.39 Tm (clearing the affected Outbox's `Data` contents is more predictable when the Outbox contains only the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 628.39 Tm (failed message.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 600.39 Tm (Step 6: Reopen Mail while still offline) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 576.39 Tm (Open Mail before reconnecting Wi-Fi or Ethernet.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 554.39 Tm (Check the following:) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 532.39 Tm (- The oversized message no longer appears in Outbox.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 515.59 Tm (- Mail stays open without the memory warning.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 498.79 Tm (- Inbox, Sent, Drafts, and any "On My Mac" mailboxes you use still appear normally.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 481.99 Tm (If everything looks right, reconnect to the network. Send yourself a small plain-text test email before) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 466.99 Tm (trying another attachment.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 444.99 Tm (Keep the Outbox backup for a little longer. Once the test message sends and Mail remains stable, you) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 429.99 Tm (can delete the quarantined data to reclaim the storage space.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 401.99 Tm (If Mail restores the bad window when you open it) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 377.99 Tm (macOS can reopen windows that were present when an app last quit. Apple documents a simple) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 362.99 Tm (one-time way to prevent that: hold Shift while opening the app.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 340.99 Tm (Quit or force quit Mail, then hold Shift while launching Mail again. This tells macOS not to restore the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 325.99 Tm (windows that were open during the previous Mail session.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 303.99 Tm (This can buy enough time to inspect the Outbox after the file cleanup, especially if Mail keeps) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 288.99 Tm (reopening the same compose or message window.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 260.99 Tm (Is Safe Mode required?) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 236.99 Tm (No evidence shows that Safe Mode is required for the Outbox file removal itself. The successful) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 221.99 Tm (Tahoe report used Safe Mode during the cleanup, but the user also indicated that it might not have been) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 206.99 Tm (necessary.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 184.99 Tm (Apple describes Safe Mode as a diagnostic startup method that helps isolate problems caused by) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 169.99 Tm (software loaded during startup. It can still be useful here when Mail or related startup behavior keeps) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 154.99 Tm (interfering with the cleanup.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 132.99 Tm (On an Apple silicon Mac:) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 110.99 Tm (1. Shut down the Mac.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 94.19 Tm (2. Hold the power button until startup options appear.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 77.39 Tm (3. Select the startup volume.) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 4 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 13 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 14 0 R >> endobj 14 0 obj << /Length 4544 >> stream BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 789.89 Tm (4. Hold Shift and click Continue in Safe Mode.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 773.09 Tm (On an Intel Mac, restart and hold Shift until the login window appears.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 751.09 Tm (Once in Safe Mode, keep Mail closed, perform the Outbox cleanup, restart normally, and test Mail) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 736.09 Tm (offline first.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 708.09 Tm (What if the message is gone from disk but Mail still shows it?) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 684.09 Tm (Apple notes that changes made to mailboxes through Finder may not immediately appear inside Mail. If) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 669.09 Tm (the stuck message has been removed from the filesystem but Mail still shows a ghost entry or) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 654.09 Tm (incorrect Outbox count, rebuild the mailbox before touching Mail's global index files.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 632.09 Tm (When Mail is stable enough to use:) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 610.09 Tm (1. Select the affected mailbox in the sidebar.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 593.29 Tm (2. Choose Mailbox > Rebuild.) Tj ET BT /F1 10.5 Tf 0.2 0.23 0.28 rg 1 0 0 1 46 576.49 Tm (3. Allow Mail to finish updating the mailbox list.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 559.69 Tm (Rebuild is an Apple-supported command for refreshing the list of messages in a mailbox.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 531.69 Tm (Last resort: rebuild Mail's Envelope Index) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 507.69 Tm (If the actual Outbox data is gone but Mail still has stale message records, counts, or repeated display) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 492.69 Tm (problems, Mail's Envelope Index may need rebuilding.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 470.69 Tm (Do this only after backing up your Mail data. Rebuilding the index affects Mail globally and can take) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 455.69 Tm (time on a large mailbox collection.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 433.69 Tm (Quit Mail, then go to:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 409.69 Tm (~/Library/Mail/V10/MailData) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 391.19 Tm (Look for files named:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 367.19 Tm (Envelope Index) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 350.315 Tm (Envelope Index-shm) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 333.44 Tm (Envelope Index-wal) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 314.94 Tm (Move those files to a temporary backup folder rather than deleting them immediately. Reopen Mail and) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 299.94 Tm (allow it to rebuild its index.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 277.94 Tm (This step is widely used for damaged Mail indexes, including Tahoe-era reports, but it should stay) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 262.94 Tm (behind the targeted Outbox cleanup. Removing the oversized message from `Outbox.mbox` addresses) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 247.94 Tm (the source of this specific freeze. Rebuilding `Envelope Index` deals with Mail's cached view of the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 232.94 Tm (mailbox afterward.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 204.94 Tm (What not to delete) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 180.94 Tm (Avoid broad cleanup advice that tells you to erase all of `~/Library/Mail/V10`, delete every account,) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 165.94 Tm (or remove random files under Mail's container folders.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 143.94 Tm (For this problem, keep the scope narrow. The affected `Outbox.mbox` is the target.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 121.94 Tm (Also avoid treating this folder as the Outbox:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 97.94 Tm (~/Library/Containers/com.apple.mail/Data/Library/Mail Downloads) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 5 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 15 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 16 0 R >> endobj 16 0 obj << /Length 4745 >> stream BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 789.89 Tm (Mail Downloads is used for local copies of attachments that you open from messages. Clearing it is a) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 774.89 Tm (different storage cleanup task and does not directly remove a queued message from the local Outbox.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 746.89 Tm (Why the message does not appear in webmail) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 722.89 Tm (Apple distinguishes mailboxes stored "On My Mac" from mailboxes stored on a mail server. An "On) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 707.89 Tm (My Mac" mailbox is local to that Mac.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 685.89 Tm (A message that is still stuck in a local Outbox may never have reached the provider's SMTP service or) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 670.89 Tm (server-side mailbox. Webmail therefore has nothing to delete. The Mac's local Mail store has to be) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 655.89 Tm (fixed first.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 633.89 Tm (This is also a useful diagnostic clue. If the message is absent from webmail but present under "On My) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 618.89 Tm (Mac" and Mail freezes while processing it, local Outbox data deserves attention before you reset the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 603.89 Tm (email account or change server settings.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 575.89 Tm (A 30 GB file is too large for Mail Drop too) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 551.89 Tm (Apple Mail can use Mail Drop for attachments that exceed a provider's normal message limit, but) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 536.89 Tm (Apple currently limits Mail Drop attachments to 5 GB.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 514.89 Tm (A 30 GB file is therefore outside Mail Drop's supported size as well. Use a file-sharing service, cloud) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 499.89 Tm (drive, NAS link, or another transfer method designed for files of that size. Send the recipient a) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 484.89 Tm (download link instead of attaching the file directly to an email.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 456.89 Tm (If the Outbox folder is missing) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 432.89 Tm (First confirm that Mail is fully quit, then search the entire Mail directory instead of assuming a) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 417.89 Tm (particular account folder:) Tj ET BT /F1 9.5 Tf 0.18 0.2 0.24 rg 1 0 0 1 54 393.89 Tm (find "$HOME/Library/Mail" -type d -name "Outbox.mbox" -print) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 375.39 Tm (If no Outbox exists and the message still appears in Mail, the problem may have shifted from stored) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 360.39 Tm (message data to Mail's index or restored application state. Try the Shift-launch method, then Mailbox >) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 345.39 Tm (Rebuild if Mail opens. The Envelope Index reset belongs after those steps.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 323.39 Tm (If the message also appears in webmail, handle it at the provider side first because that indicates the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 308.39 Tm (message or queue is no longer purely local.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 280.39 Tm (If there are several Outbox.mbox folders) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 256.39 Tm (Do not clear them all.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 234.39 Tm (Compare their sizes with `du -sh`, inspect modification times in Finder, and identify the one that grew) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 219.39 Tm (when the oversized message was created. A 30 GB attachment gives you a useful clue because the) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 204.39 Tm (affected Outbox may be dramatically larger than the others.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 182.39 Tm (When the size difference is unclear, back up each candidate before changing anything and work on) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 167.39 Tm (one Outbox at a time.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 139.39 Tm (Why deleting the message in Mail can fail to stick) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 6 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj 17 0 obj << /Type /Page /Parent 2 0 R /MediaBox [0 0 595.28 841.89] /Resources << /Font << /F1 3 0 R /F2 4 0 R >> >> /Contents 18 0 R >> endobj 18 0 obj << /Length 2398 >> stream BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 789.89 Tm (Deleting a message through Mail's interface still requires Mail to update its local mailbox data and) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 774.89 Tm (indexes. If the app runs out of memory or is force-quit before that update finishes, the deletion may) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 759.89 Tm (never be committed. The same queued message is then available again the next time Mail opens and) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 744.89 Tm (processing starts over.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 722.89 Tm (Filesystem cleanup works around that loop by removing the local queued data while Mail is not running.) Tj ET BT /F2 15 Tf 0.08 0.1 0.14 rg 1 0 0 1 46 694.89 Tm (The safest order to follow) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 670.89 Tm (For a stuck oversized Outbox message on macOS Tahoe, start offline and try the normal delete once.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 655.89 Tm (If Mail freezes or the message returns, quit Mail and remove the affected `Outbox.mbox` data while) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 640.89 Tm (keeping a backup. Reopen Mail offline, test it, then reconnect.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 618.89 Tm (Use Shift-launch or Safe Mode when Mail keeps restoring the problem state. Use Mailbox > Rebuild for) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 603.89 Tm (a stale mailbox view. Rebuild `Envelope Index` only when the message data has already been removed) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 588.89 Tm (and Mail still shows bad index information.) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 566.89 Tm (I recommend keeping the quarantined Outbox data until you have reopened Mail, checked your local) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 551.89 Tm (mailboxes, and successfully sent a small test message. Once those checks pass, delete the backup copy) Tj ET BT /F1 11 Tf 0.14 0.16 0.2 rg 1 0 0 1 46 536.89 Tm (and empty the Trash if you want the disk space back.) Tj ET q 0.86 0.88 0.92 RG 1 w 46 42 m 549.28 42 l S Q BT /F1 8.4 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 30 Tm (TechRounder | Page 7 of 7) Tj ET BT /F1 7.2 Tf 0.42 0.45 0.5 rg 1 0 0 1 46 19 Tm (https://www.techrounder.com/pdf/blog/how-to-delete-a-stuck-outbox-email-that-freezes-apple-mail-on-macos-tahoe.pdf) Tj ET endstream endobj xref 0 19 0000000000 65535 f 0000000015 00000 n 0000000064 00000 n 0000000161 00000 n 0000000231 00000 n 0000000306 00000 n 0000000448 00000 n 0000005416 00000 n 0000005558 00000 n 0000010206 00000 n 0000010349 00000 n 0000015154 00000 n 0000015298 00000 n 0000020407 00000 n 0000020551 00000 n 0000025147 00000 n 0000025291 00000 n 0000030088 00000 n 0000030232 00000 n trailer << /Size 19 /Root 1 0 R >> startxref 32682 %%EOF