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Since you mentioned SSL issues, is your laptop where you trying the upload behind a firewall. It could be the firewall is causing the upload error. If possible, try disabling firewall and retry
Based on the information provided, it seems that the issue you're experiencing is not likely related to AWS itself, but rather to your local setup or network configuration. Since the problem started after upgrading your laptop, it's possible that there's a compatibility issue or a configuration change that's affecting your ability to upload larger files.
Here are a few suggestions to troubleshoot and potentially resolve the issue:
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Check your AWS CLI version and update it if necessary. The new laptop might have a different version installed, which could be causing the SSL/timeout error you encountered.
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Verify that your laptop's date and time settings are correct and synced. Incorrect time settings can sometimes cause SSL issues.
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Try adjusting the multipart upload settings in your AWS CLI configuration. You can modify parameters like multipart_threshold and multipart_chunksize to see if it helps with larger file uploads.
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Enable versioning on your S3 bucket. While this may not directly solve the upload issue, it can help you track changes and potentially identify any problems with object versions.
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Check if there are any security software or settings on your new laptop that might be interfering with the upload process for larger files.
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Test uploading through a VPN to rule out any potential ISP or routing issues that might have coincidentally started after your laptop upgrade.
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If possible, try uploading from your old laptop again to confirm if the issue is indeed related to the new hardware.
If none of these solutions work, you may want to contact AWS support for further assistance, as there could be an underlying issue that's not immediately apparent. They can help you investigate any potential account-specific or regional problems that might be affecting your uploads.
Sources
Unable to upload to S3 bucket | AWS re:Post
Failed to upload file to s3 | AWS re:Post
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- asked a year ago

Hi there, did you ever find a solution to this problem? I am having the exact same issue on my Mac. I simply can't upload to S3 - either via API, CLI, or the console. tiny files are fine but larger fails fail, except for 1/10 times where it succeeds.