The system cannot find file path specified when sending email with attachments happens randomly

Question

The system cannot find file path specified when sending email with attachments happens randomly

Wan Khoo 0

Issue: When sending emails with email attachments, there will be an error that prevents user from sending. Does not matter where the file is attached from. eg. downloads or documents. It is as though Outlook app couldn't recognize the file path. Weirdly it does not happen consistently, drafting another same exact email and attaching the same attachments right after the issue happens does not warrant the issue to happen again.

Error: The system cannot find the file specified.

Austin-H 6,990 Reputation points Microsoft External Staff Moderator

2025-08-14T06:58:13.5466667+00:00

Hi @Wan Khoo

It has been a while since your last approach.

May I know if Nghia's suggestions worked on your scenario?

I am looking forward if there is any new update from your end.

2 answers

Your answer

Austin-H 6,990 Reputation points Microsoft External Staff Moderator

2025-08-14T06:58:13.5466667+00:00

Hi @Wan Khoo

It has been a while since your last approach.

May I know if Nghia's suggestions worked on your scenario?

I am looking forward if there is any new update from your end.

Answer 1

Matthew-P 7,535 Microsoft External Staff Moderator

Hi Wan Khoo,

Welcome to Microsoft Q&A Forum!

Have a good day and I hope you're doing well!

Thank you for reaching out to us. I’m sorry for the inconvenience caused by the “The system cannot find file path specified” error in Outlook. This issue can be triggered by several factors, such as incorrect file paths, incompatible add-ins, or system misconfigurations.

Below are some step-by-step troubleshooting methods you can try:

Repair the Outlook Application

Close Outlook completely.
Press Windows + R, type appwiz.cpl, and press Enter to open Programs and Features.

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Locate Microsoft Office in the list, right-click it, and select Change.

4 Choose Quick Repair and click Repair. Wait for the process to finish.

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If the issue persists, repeat the steps and select Online Repair.

Check and Set Default Apps by File Type

Go to Start > Settings > Apps > Default Apps.
Scroll down and select Choose default apps by file type.

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Find the file types you usually attach (e.g., .pdf, .docx, .xlsx, .jpg, .png).

4 Click the app next to each file type and select the appropriate program (e.g., Adobe Reader for .pdf, Microsoft Word for .docx).

User's image 5. Close the window and try attaching files again in Outlook.

To assist you better, could you please provide some additional information?

What type of file(s) are you usually attaching when the error occurs (e.g., PDF, Word, Excel, images, etc.)?
If possible, please let me know the approximate file size(s) that trigger the error.
Since the issue does not happen every time, do you notice any differences between the times when the error occurs and when it does not? (For example: file location, file type, file size, or any other details.)

Additionally, please check that both your Windows and Outlook applications are updated to the latest versions, as this can help prevent compatibility issues.

Once again, I sincerely apologize for the inconvenience this issue has caused, as I understand it impacts your work efficiency. Please know that I am here to support you, and we will work through this problem together. I truly appreciate your effort and patience throughout this process.

Please note, these recommendations are based on my testing environment. If there’s any information I may have misunderstood, or if you need further clarification or details on any step, feel free to let me know. I’m here to help!

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment". User's image Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Wan Khoo 0 Reputation points

2025-08-04T05:40:14.8133333+00:00
Hi Nghia,

Thanks for the recommendations.

I have done the repair and app association but issue still occurs.

To answer your questions:

It happens to all file types - excel, pdf, word, msg

File size varies - no specific size that triggered the issue.

It could be from an online location (SharePoint) or locally downloaded files from documents or desktop.

Just to give some context - I am managing 30 or so computers and it is currently happening to majority of them. Not sure if this is a contributing factor - all of the computers has files (desktop, documents, pictures) backed up to OneDrive.

It started a month ago when it was only happening to a few of them, but right now it seems to have propagate to majority of the computers.

There was an instance where the email does not even have any attachments and it still gives the same error. Not sure if this is helpful, this email was left unattended for 30 or so mins (minimized), when the user realized that it was still unfinished and tried sending after finishing it, it gave that error as soon as the send button is clicked.

It is not as though the email window is unresponsive, everything works fine except for the send function. It will give the same error if it is clicked on again. User has been doing copy pasting on a new email to send it out if error occurs.
Matthew-P 7,535 Reputation points Microsoft External Staff Moderator

2025-08-07T09:41:21.7833333+00:00
Hi Wan Khoo,

Thank you for your continued patience and for sharing those additional details. It's clear this issue is causing significant disruption, especially with it affecting the majority of your 30+ computers and even emails without attachments after they've been left minimized. I'm truly sorry for the frustration and inconvenience this has caused, as I know it impacts your daily workflow and management of multiple systems. I appreciate you trying the previous steps and providing context like the OneDrive backups and the inconsistent nature of the error. We're making progress, and I'm committed to helping you resolve this step by step.

Since the earlier troubleshooting hasn't fully resolved it, let's try some more targeted steps that have helped in similar cases reported on Microsoft forums and support articles. These focus on clearing Outlook's secure temp folder and checking for system-level corruptions. As this affects multiple machines, I recommend testing on just one or two first to minimize disruption. Important: Before proceeding, back up any important data and your registry (via regedit > File > Export). If you're not comfortable editing the registry, consider consulting an IT admin or skipping to the system scans.

Clear the Outlook Secure Temporary Folder: This is one of the most frequent fixes for attachment-related errors, as accumulated temp files can cause conflicts.

Open the Registry Editor: Press Windows key + R, type regedit, and press Enter. (Run as administrator if prompted.)

Navigate to: HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Security (Replace 16.0 with your Outlook version, e.g., 15.0 for Outlook 2013 or 14.0 for 2010.)

In the right pane, find the value named OutlookSecureTempFolder. Note the path listed (it's usually something like C:\Users\YourUsername\AppData\Local\Microsoft\Windows\Temporary Internet Files\Content.Outlook\RandomFolder).

Open File Explorer and paste that path into the address bar to navigate to the folder.

Delete all files inside this folder (but not the folder itself). If prompted, confirm permissions or run File Explorer as administrator.

Close and restart Outlook, then try attaching and sending an email again. Also, test a no-attachment draft: Create an email, minimize it for 30 minutes, then finish and send.

If the registry entry is missing or incorrect, you can recreate it by double-clicking OutlookSecureTempFolder and setting it to a valid path like %USERPROFILE%\AppData\Local\Temp\Temporary Internet Files\Content.Outlook\.

Run System File Checker (SFC) and CHKDSK Scans: These check for and repair corrupted system files or disk errors that might affect file access.

Open Command Prompt as Administrator: Search for cmd in Start, right-click, and select Run as administrator.

Run sfc /scannow and wait for it to complete (it may take 10-30 minutes).

Then, run chkdsk C: /f /r (replace C: with the drive where your files or Outlook is installed). If prompted, type Y to schedule on restart, then reboot your computer.

After the restart, open Outlook and test sending emails with and without attachments, including the 30-minute minimized draft scenario.

Once again, I sincerely apologize for the ongoing challenges this presents, especially in a multi-machine environment like yours. I truly value your effort in troubleshooting and am here to support you every step of the way. These recommendations are based on common resolutions from Microsoft support resources, but if they don't fully address it, we can escalate to a dedicated Microsoft Support ticket for enterprise-level assistance.

Please let me know how it goes or if you need clarification on any step. I'm just a reply away!
Matthew-P 7,535 Reputation points Microsoft External Staff Moderator

2025-08-08T08:01:38.6766667+00:00

Hi Wan Khoo,

We’d love to hear back from you whenever you're ready.

If you feel this helped point you in the right direction, you're more than welcome to mark it as "Accepted Answer". This helps me keep track of your case and continue supporting you as best I can. This can make it easier for others facing a similar issue to find their way to a solution, too.If there’s any update, please don’t hesitate to let us know.
Matthew-P 7,535 Reputation points Microsoft External Staff Moderator

2025-08-11T08:42:35.56+00:00

Hi Wan Khoo,

Have a good day and I hope you're doing well!

Would you mind getting back to us when it’s convenient for you?

Your feedback is important for us to continue troubleshooting effectively.

If you need further assistance, please share more details so we can provide the most accurate support possible.

Answer 2

Wan Khoo 0

Hi Nghia,

I’ve cleared the Outlook Secure Temporary File folder and have also run both SFC and CHKDSK. Since the issue occurs intermittently, I can’t confirm yet whether it has been fully resolved.

I’ll continue to monitor the situation over the next few weeks and will update you once I’m more certain of the outcome.

Matthew-P 7,535 Reputation points Microsoft External Staff Moderator

2025-08-14T09:02:57.99+00:00

Hi Wan Khoo,

Thank you for trusting and trying my method! Please continue to monitor the situation over the next few weeks. If there are any changes (whether it improves or if issues persist), feel free to comment back and let me know. I'll continue to support you as much as I can.

In the meantime, if my initial answer has been even partially helpful, please consider marking it as “Accepted Answer” so others facing similar issues can find it more easily.

This helps others in the community too. Thanks for your understanding and support!
Matthew-P 7,535 Reputation points Microsoft External Staff Moderator

2025-09-08T02:11:18.59+00:00

Hi Wan Khoo,

Have a good day and long time no see!

It's been a few weeks since your last update on this issue. We wanted to follow up and check in: Is everything working smoothly now, and has the problem been fully resolved?

If you still need any assistance or have additional questions, feel free to reply here. I am looking forward if there is any new update from your end.

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The system cannot find file path specified when sending email with attachments happens randomly

2 answers

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