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Scan for outdated or missing drivers - takes under a minuteDriver Scan →Repair Windows errors before they cause bigger problemsFix Now →Fix the driver behind crashes, sound loss and screen glitchesFind Drivers →To share a file in live chat, open the chat composer, select its paperclip or attachment control, choose the file, review it if a preview appears, and send or confirm the upload. The exact control and restrictions depend on the chat platform and channel: a file may be too large, use an unsupported format, or be blocked until an administrator enables attachments.
How to attach a file in a live chat
- Open the conversation and look beside the message box for a paperclip, attachment, file, or paper icon. The label and position vary by chat product.
- Select the control and choose the file or image from your device. If the platform allows multiple attachments, select the files you want to send.
- Review the pending attachment or preview, if one appears. Check that you chose the intended file and that the platform has not displayed a size or format error.
- Choose Send, Upload, or the confirmation control shown by the chat. Some platforms ask you to confirm the upload after you click Send.
- Wait for the message or file link to appear in the conversation before closing the chat. If the attachment is rejected, use the troubleshooting steps below rather than repeatedly trying the same file.
For example, LiveChat’s documented flow is to click the paperclip in the chat area, choose the files, review the pending selection, click Send, and then confirm Upload file. A customer uses the paper icon beside the text area, selects one or more files, reviews the preview, and confirms. LiveChat also documents pasting a file from the clipboard or dragging and dropping it into the chat. These are LiveChat-specific options, not universal live-chat controls. LiveChat: Sharing files over LiveChat
In a Microsoft Dynamics 365 Customer Service live-chat widget, customers use the Attach control. Microsoft says drag-and-drop is not supported in that widget. Microsoft Learn: Configure file attachment capability for a chat widget
Why an attachment may not work
Attachment support is not one universal feature with one universal file limit. It can vary by product, channel, direction (customer-to-agent or agent-to-customer), and administrator configuration. Check these points when the chat will not accept a file:
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- Attachment sharing may be disabled. The platform administrator may need to enable it. LiveChat has separate customer and agent file-sharing settings; Microsoft documents administrator-controlled attachment capability for its widget. LiveChat file sharing settings · Microsoft widget attachment configuration
- The file may exceed the product’s limit. Limits differ, and some settings are configurable. Do not assume that a limit from another service or channel applies to this conversation.
- The extension may not be accepted in that channel. A type supported in one channel may be blocked in another. Some systems let administrators define allowed types.
- The system may block the file for security reasons. Microsoft documents rejection of unsupported, oversized, or malicious files. LiveChat says potentially threatening files are filtered; an agent may be able to get access to a flagged customer upload or discard it. Microsoft Learn · LiveChat Help Center
- The method may not be supported. If drag-and-drop fails, use the attachment control; Microsoft specifically says drag-and-drop is not supported in its live-chat widget.
Try a smaller file in a format the service accepts, or ask the agent or administrator whether attachments are enabled for your conversation. For Microsoft WhatsApp messages, Microsoft recommends converting certain document attachments to PDF. That is a channel-specific workaround, not a guarantee that every chat accepts PDFs. Microsoft Learn: Support for live chat and asynchronous channels
File-size and format limits vary by platform
These examples come from the vendors’ documentation and refer to different products and contexts. They are not interchangeable limits for live chat generally.
| Platform and context | Documented limit or formats | What to know |
|---|---|---|
| LiveChat file sharing | Up to 10 MB per file; the help page lists JPEG, PNG, and GIF among supported chat image formats. | LiveChat’s help page was updated April 28, 2025. It also describes clipboard paste and drag-and-drop. LiveChat Help Center |
| Zendesk chat | 20 MB; default file types listed include PDF, PNG, JPEG, GIF, and TXT. | The cited Zendesk guide was edited May 1, 2026. Files are shared as links, and anyone with the URL can access the chat file. Zendesk: Sending files in a chat |
| Microsoft Dynamics 365 live-chat widget | Administrators can configure allowed types and size limits; live-chat image files have a maximum size of 20 MB in the configuration documentation. | Accepted attachment formats depend on the channel. Microsoft documents different channel support for Teams, Apple Messages for Business, Facebook, LINE, WhatsApp variants, SMS, and custom messaging. Widget configuration · Channel support |
| Salesforce Enhanced Chat | Up to five attachments, each up to 5 MB, in one conversation update. | Customers can preview BMP, GIF, JPG, JPEG, PNG, and PDF; other supported file types do not preview in the conversation window. Salesforce: Enhanced Chat considerations and limitations · Salesforce: Send images and files in messaging sessions |
A file that uploads successfully may still appear only as a downloadable attachment rather than an inline preview. Preview support is a separate platform feature: Salesforce Enhanced Chat, for example, previews the image and PDF types listed above, not every supported file type. LiveChat documents opening supported images such as JPEG, PNG, and GIF in a lightbox. Salesforce Help · LiveChat Help Center
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Protect your privacy when sharing a file
Before sending sensitive material, consider how the service makes an attachment available and who can open it. Zendesk warns that anyone with a chat attachment URL can access the file, regardless of authentication settings. Treat such a link as shareable by anyone who obtains it; do not assume the chat login protects the attachment itself. Zendesk: Sending files in a chat
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What to check before relying on chat attachments
If you are choosing a chat service or setting expectations for customers, compare the details that affect whether a file can be sent, viewed, and kept private:
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- Maximum size per file and, if documented, per message or conversation update.
- Accepted file types for the exact channel and direction of transfer.
- Whether an administrator must enable attachments, and whether customer and agent permissions are separate.
- Which images or documents show an inline preview and which are download-only.
- Whether attachment links require authentication, who can access them, how long they remain available, and whether they can be revoked.
- What scanning, filtering, or warning process applies to blocked or flagged files.
Use the vendor’s current documentation and the settings for the specific deployment for numeric limits and allowed formats; a channel-level table or configurable limit can differ from the product’s general description.
Frequently Asked Questions
Can I send more than one file in a live chat?
It depends on the product and its configuration. LiveChat documents selecting one or more files. Salesforce Enhanced Chat allows customers to send up to five attachments in one conversation update, each no larger than 5 MB. LiveChat Help Center · Salesforce Help
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Upload support and inline preview support are different. The file may be available as an attachment or download even when the chat does not display it as an image preview. Salesforce Enhanced Chat’s preview list includes BMP, GIF, JPG, JPEG, PNG, and PDF, while other supported types do not preview in the conversation window. Salesforce Help
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Is it safe to send a private document through live chat?
Check the specific platform’s attachment access and retention behavior first. In Zendesk chat, anyone with the attachment URL can access that file, even if authentication is enabled. Do not send a sensitive document through a service unless its access controls meet your needs. Zendesk Help
What should I do if the chat says a file is unsupported?
Check the extension and size against that platform’s rules, confirm attachments are enabled, and use the chat’s attachment control rather than an unsupported transfer method. If the channel accepts a different document format, convert the file only when that preserves the information the recipient needs; Microsoft specifically recommends PDF for certain document attachments sent through WhatsApp. Microsoft Learn
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Frequently Asked Questions
Can I send more than one file in a live chat?
It depends on the product and its configuration. LiveChat documents selecting one or more files. Salesforce Enhanced Chat allows customers to send up to five attachments in one conversation update, each no larger than 5 MB.
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Why can I upload an image but not see it in the chat?
Upload support and inline preview support are different. The file may be available as an attachment or download even when the chat does not display it as an image preview. Salesforce Enhanced Chat previews BMP, GIF, JPG, JPEG, PNG, and PDF; other supported types do not preview in the conversation window.
Is it safe to send a private document through live chat?
Check the specific platform’s attachment access and retention behavior first. In Zendesk chat, anyone with the attachment URL can access that file, even if authentication is enabled.
What should I do if the chat says a file is unsupported?
Check the extension and size against that platform’s rules, confirm attachments are enabled, and use the chat’s attachment control rather than an unsupported transfer method. Microsoft recommends PDF for certain document attachments sent through WhatsApp.
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