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To share a file in live chat, open the attachment or paperclip control beside the message box, choose the file, review it if a preview appears, and select Send or the platform’s confirmation button. The exact controls, file limits, supported formats, and privacy behavior depend on the chat service and channel. If you do not see an attachment control, file sharing may be disabled by the organization.
How to attach a file in a live-chat conversation
- Open the chat composer. Look beside the message field for a paperclip, attachment, or file icon. Some chat widgets use a paper-shaped icon.
- Select the file or image. Choose it from your device. If the service displays a pending attachment or preview, check that it is the correct item before sending.
- Send and confirm. Select Send or the button that confirms the upload. Some systems ask you to confirm separately after selecting files.
- Check the conversation for the result. Depending on the service, the recipient may see an inline image or document preview, or a link to open or download the file.
These are general steps, not a guarantee that every chat widget supports attachments. For example, LiveChat documents clipboard paste and drag-and-drop as additional ways to attach files; Microsoft says drag-and-drop is not supported in its live-chat widget. LiveChat’s file-sharing instructions and Microsoft’s chat-widget configuration documentation describe those product-specific behaviors.
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How file sharing works in specific chat platforms
LiveChat
In a LiveChat conversation, select the paperclip in the chat area, choose one or more files, review the pending selection, select Send, and confirm Upload file. Customers use the paper icon next to the text area, choose the files, review the preview, and confirm. LiveChat also documents pasting a file from the clipboard or dragging and dropping it into the chat. Each file can be up to 10 MB, according to its help page updated April 28, 2025. The page lists JPEG, PNG, and GIF as supported image formats. After upload, both participants receive a link; the file is also available later in Archives and the transcript. See LiveChat’s instructions and settings.
Microsoft Dynamics 365 Customer Service live chat
Customers use the chat widget’s Attach control when the organization has enabled attachments. Administrators can configure whether attachments are allowed and set restrictions. Microsoft says the widget does not support drag-and-drop. Unsupported file types, oversized files, and files identified as malicious are rejected with an error. Its configuration documentation gives a maximum of 20 MB for live-chat image files; other accepted types and limits depend on the configuration and channel. Microsoft’s configuration guide covers the widget, while its channel documentation explains how attachment support varies across channels.
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Zendesk chat
Zendesk’s cited guide gives a 20 MB file limit and lists PDF, PNG, JPEG, GIF, and TXT as default accepted types. Files are shared as links rather than necessarily appearing as inline previews. Zendesk warns that anyone with an attachment URL can access that file, regardless of the chat’s authentication settings. Read Zendesk’s file-sharing guidance for its current instructions and access warning; the page was edited May 1, 2026.
Salesforce Enhanced Chat
Salesforce documents a limit of five attachments in one Enhanced Chat conversation update, with each attachment up to 5 MB. Customers can preview BMP, GIF, JPG, JPEG, PNG, and PDF files in the conversation window. Other supported file types may upload without an inline preview. These figures and preview details apply to the documented Salesforce chat context, not to every Salesforce messaging channel. Salesforce’s messaging-session file guide and Enhanced Chat limitations provide the relevant details.
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Limits and behavior differ by platform
The examples below are not competing measurements of one universal limit. They refer to different products and, in Microsoft’s case, settings and channels. Check the documentation for the particular chat widget and direction of the message before relying on a limit.
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| Platform and context | Documented limit | Formats or preview details | Important behavior |
|---|---|---|---|
| LiveChat | Up to 10 MB per file; LiveChat Help Center page updated April 28, 2025. | The help page lists JPEG, PNG, and GIF images; images can open in a lightbox. | Paste and drag-and-drop are documented. Uploaded files produce links available later in Archives and transcripts. LiveChat Help Center. |
| Zendesk chat | 20 MB; Zendesk Help page edited May 1, 2026. | Default list includes PDF, PNG, JPEG, GIF, and TXT. | Files are shared by link; anyone with the URL can access the file. Zendesk Help. |
| Microsoft Dynamics 365 live-chat widget | Live-chat image files have a 20 MB maximum in the configuration documentation. Other limits depend on administrator configuration and channel. | Accepted formats vary across channels; the channel documentation lists distinct support for Teams, Apple Messages for Business, Facebook, LINE, WhatsApp variants, SMS, and custom messaging. | Administrators control attachment capability and restrictions. Drag-and-drop is not supported in the live-chat widget. Configuration and channel support. |
| Salesforce Enhanced Chat | Up to five attachments in one conversation update, each up to 5 MB. | Preview documented for BMP, GIF, JPG, JPEG, PNG, and PDF; other supported types do not preview in the conversation window. | The documented cap and preview rules are for Enhanced Chat. Salesforce Help and Enhanced Chat limitations. |
Why an attachment may not send
- There is no attachment icon. The organization may not have enabled file sharing, or the selected chat channel may not support it. Microsoft’s widget configuration makes attachment capability administrator-controlled; LiveChat also has separate customer and agent sharing settings. Microsoft configuration; LiveChat sharing settings.
- The file exceeds a size limit. Check the per-file cap and, where applicable, the number of files allowed in one message. Limits vary: LiveChat documents 10 MB per file, Zendesk 20 MB, and Salesforce Enhanced Chat up to five files of 5 MB each per conversation update.
- The extension or format is unsupported. Accepted types can differ by platform and channel. Microsoft’s documentation gives channel-specific format information, and administrators can set allowed types for its live-chat widget. Use a supported format; Microsoft specifically recommends converting certain document attachments to PDF for WhatsApp messages. Microsoft channel documentation.
- The service blocked the upload. Unsupported or oversized files can be rejected, and security checks may block a file identified as malicious. Microsoft documents rejection for unsupported, oversized, or malicious files; LiveChat says potentially threatening files are filtered.
- You expected a preview, but see a link or download instead. A successful upload does not guarantee an inline preview. Salesforce Enhanced Chat previews certain image formats and PDF, while other supported file types do not preview in the conversation window. Zendesk describes attachments as links.
- Drag-and-drop does nothing. Use the attachment control instead. LiveChat supports drag-and-drop, but Microsoft’s live-chat widget does not.
Protect sensitive files before sharing
Do not assume a chat attachment is private just because the conversation requires authentication. Zendesk explicitly says anyone with the attachment URL can access the file, regardless of authentication settings. LiveChat describes a different workflow: potentially threatening customer uploads can be flagged, and an agent can choose to get access or discard the file; discarded links cannot be opened by agents, including from Archives. These are product-specific behaviors, so check the applicable platform’s access, retention, and security rules before sending sensitive information. Zendesk’s warning; LiveChat’s filtering details.
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What to check when choosing or configuring chat file sharing
- Size: Confirm both the maximum per file and any per-message or per-update attachment count.
- Formats and channel: Check allowed file types for the specific channel and whether the rule differs for customer uploads versus agent attachments.
- Enablement and permissions: Confirm that sharing is enabled and whether customers and agents have separate permissions.
- Previews: Find out which image and document formats display inline and which are links or downloads.
- Link access and retention: Determine who can open an attachment URL, how long it remains available, and whether it can be revoked.
- Security handling: Check what happens when a file is flagged or rejected and what users see when an upload fails.
Vendor documentation is the controlling source for platform-specific limits and behavior because administrators can configure some settings and channel support can differ. LiveChat provides its sharing procedure and settings at its Help Center; Microsoft documents widget configuration and channel differences; Zendesk documents chat attachments; and Salesforce documents messaging-session files and Enhanced Chat limitations.
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Can I drag and drop a file into live chat?
It depends on the chat widget. LiveChat documents drag-and-drop; Microsoft says it is not supported in its live-chat widget. If it fails, use the attachment control beside the message field.
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Why did my image upload but not appear in the conversation?
Some platforms show attachments as links or downloads rather than inline previews. Preview support also depends on the file format and chat product; for example, Salesforce Enhanced Chat previews specified image formats and PDF, but not every supported file type.
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That depends on the platform. LiveChat says uploaded files are available later in Archives and the transcript. Zendesk says anyone with an attachment URL can access the file. Consult the service’s rules before sharing information that should not remain accessible by link.
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What should I do if live chat rejects a document?
Check the file’s size and format against the service’s limits, confirm that attachments are enabled, and check whether the channel supports that type. For WhatsApp messages in the documented Microsoft context, Microsoft recommends converting certain document attachments to PDF.
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