A Microsoft digital storytelling app for creating and sharing interactive reports and presentations.
Hi @Admin,
Thank you for reaching out to the Microsoft Q&A forum and for clearly outlining your concern.
From your description, the Upload image option in Sway has shown a “try again later” message since Thursday and Sway takes about five minutes to open each time. I truly understand and appreciate the effort you have made retrying over several days, especially because timely newsletters and class materials are essential in an education setting.
In many school tenants, this behavior can arise when a temporary Microsoft 365 service incident overlaps with local factors such as browser cache or extensions, as well as network or policy controls that limit Sway media endpoints and content sources. Moreover, Sway’s admin settings can restrict external content or disable the service for certain licenses, which directly affects the Insert and Upload options you see. Consequently, stale cache or blocked endpoints can also slow Sway’s startup while it attempts to load required resources.
Below are some workable options that might be the most appropriate for your current situation:
1/ Refresh the browser environment and test a clean session
- First, clear cached site data: in Microsoft Edge go to Settings > Privacy, search, and services > Clear browsing data > Choose what to clear, set Time range to All time, then select Cookies and other site data and Cached images and files, and select Clear now. This ensures any corrupted session data is removed. View and delete browser history in Microsoft Edge - Microsoft Support
- Next, open an InPrivate window and sign in at sway.office.com to test image upload in a fresh profile without extensions. InPrivate reduces interference from stored cookies and extensions during troubleshooting.
- Then, try inserting a small JPG or PNG and observe whether Insert > Image > Upload is available. If it works InPrivate, re‑open your normal window and re‑enable extensions gradually to identify any that interfere. For ongoing performance, keeping cache healthy and testing in a private session is a recommended first diagnostic step.
- Or Upload images to OneDrive first, then insert them into Sway.
2/ Repair Sway
In the search box on the taskbar, enter control panel and select Control Panel from the results.
- Select Programs > Programs and Features.
- Right-click the program > select Repair, or if that’s not available, select Change. Then follow the directions on the screen.
Note that you need have admin permission to repair if your device is managed by organization.
3/ Uninstall and reinstall Office:
You can find guidance for uninstalling and reinstalling Office here:
Uninstall Microsoft 365 from a PC - Microsoft Support
Download, install, or reinstall Microsoft 365 or Office 2024 on a PC or Mac - Microsoft Support
4/ Isolate the network and contact IT's admin
Since your account is managed by your school, please contact your IT administrator to review your permissions and policies.
- Additionally, test on another network such as a mobile hotspot. If upload and load time improve, the issue is likely related to network filtering or proxy inspection on the school network.
- Next, ask your IT team to review your firewall or web filter allow‑lists against Microsoft’s Microsoft 365 URLs and IP address ranges so the required domains for Microsoft 365 web apps and content delivery are reachable with minimal latency. This is the authoritative catalog admins should follow.
- Finally, your IT team can run the Microsoft 365 network connectivity test to identify bottlenecks from your location and confirm healthy connectivity paths to Microsoft services.
- Reference: Microsoft 365 URLs and IP address ranges - Microsoft 365 Enterprise | Microsoft Learn
- If the issue persists after these checks, ask your IT administrator to submit a support request directly to Microsoft Support team. They can raise a support ticket by visiting: Get support - Microsoft 365 admin | Microsoft Learn
As community moderators, we appreciate your understanding that our access to internal development details is limited. Our primary role is to guide users toward the appropriate resources and support channels. While we may not have visibility into deeper backend analysis, we’ll continue doing our best to support you within the scope of our responsibilities.
I hope this information is helpful. Please follow these steps and let me know if it works for you. If you have any updates regarding the issue, please feel free to share them with me.
Thank you for your patience and your understanding. I look forward to continuing the conversation.
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