diff --git a/KMART/Commands/Kmart.swift b/KMART/Commands/Kmart.swift
index 0a8f19b..503a729 100644
--- a/KMART/Commands/Kmart.swift
+++ b/KMART/Commands/Kmart.swift
@@ -54,7 +54,8 @@ struct Kmart: AsyncParsableCommand {
         PrettyPrint.print(apiString)
 
         PrettyPrint.printHeader("GENERATING REPORTS")
-        let reportPrefix: PrettyPrint.Prefix = configuration.slack.enabled ? .default : .ending
+        let notificationsEnabled: Bool = configuration.slack.enabled || configuration.discord.enabled
+        let reportPrefix: PrettyPrint.Prefix = notificationsEnabled ? .default : .ending
         let reportStart: Date = Date()
         let reports: Reports = Reporter.generateReports(from: objects, using: configuration)
         reports.saveToDisk(using: configuration)
@@ -68,7 +69,17 @@ struct Kmart: AsyncParsableCommand {
             await Slacker.send(reports, using: configuration)
             let slackEnd: Date = Date()
             let slackString: String = String(format: "Total Time: %.1f seconds", slackEnd.timeIntervalSince(slackStart))
-            PrettyPrint.print(slackString, prefix: .ending)
+            let slackPrefix: PrettyPrint.Prefix = configuration.discord.enabled ? .default : .ending
+            PrettyPrint.print(slackString, prefix: slackPrefix)
+        }
+
+        if configuration.discord.enabled {
+            PrettyPrint.printHeader("SENDING VIA DISCORD")
+            let discordStart: Date = Date()
+            await Discorder.send(reports, using: configuration)
+            let discordEnd: Date = Date()
+            let discordString: String = String(format: "Total Time: %.1f seconds", discordEnd.timeIntervalSince(discordStart))
+            PrettyPrint.print(discordString, prefix: .ending)
         }
     }
 }
diff --git a/KMART/Helpers/Discorder.swift b/KMART/Helpers/Discorder.swift
new file mode 100644
index 0000000..70fb2f2
--- /dev/null
+++ b/KMART/Helpers/Discorder.swift
@@ -0,0 +1,150 @@
+//
+//  Discorder.swift
+//  KMART
+//
+
+import Foundation
+
+/// Struct used to perform all **Discord** operations.
+struct Discorder {
+
+    /// Send a Discord message with attached reports.
+    ///
+    /// - Parameters:
+    ///   - reports:       The reports to send via Discord.
+    ///   - configuration: The configuration containing Discord settings.
+    static func send(_ reports: Reports, using configuration: Configuration) async {
+        let discord: DiscordConfiguration = configuration.discord
+
+        PrettyPrint.print("Sending Report(s) via Discord")
+
+        await message(discord)
+
+        for attachment in discord.attachments {
+            if let data: Data = reports.data(type: attachment, using: configuration) {
+                await upload(data, of: attachment, for: discord)
+            }
+        }
+    }
+
+    /// Send a Discord message.
+    ///
+    /// - Parameters:
+    ///   - discord: The Discord configuration.
+    private static func message(_ discord: DiscordConfiguration) async {
+
+        guard let url: URL = URL(string: discord.webhookURL) else {
+            PrettyPrint.print("Invalid Discord webhook URL: \(discord.webhookURL)", prefixColor: .red)
+            return
+        }
+
+        var request: URLRequest = URLRequest(url: url)
+        request.httpMethod = "POST"
+        request.setValue("application/json; charset=UTF-8", forHTTPHeaderField: "Content-Type")
+        request.httpBody = messageData(for: discord)
+
+        do {
+            let (_, response): (Data, URLResponse) = try await URLSession.shared.data(for: request)
+
+            guard let httpResponse: HTTPURLResponse = response as? HTTPURLResponse else {
+                PrettyPrint.print("Unable to get response from Discord webhook URL: \(url)", prefixColor: .red)
+                return
+            }
+
+            // Discord returns 204 No Content on success for message-only posts
+            guard httpResponse.statusCode == 200 || httpResponse.statusCode == 204 else {
+                let string: String = HTTP.errorMessage(httpResponse.statusCode, for: url)
+                PrettyPrint.print(string, prefixColor: .red)
+                return
+            }
+        } catch {
+            PrettyPrint.print(error.localizedDescription, prefixColor: .red)
+        }
+    }
+
+    /// Generate HTTP body data for the Discord message.
+    ///
+    /// - Parameters:
+    ///   - discord: The Discord configuration.
+    /// - Returns: A `Data` object if successful, otherwise `nil`.
+    private static func messageData(for discord: DiscordConfiguration) -> Data? {
+        let dictionary: [String: Any] = [
+            "content": discord.text
+        ]
+
+        guard let data: Data = try? JSONSerialization.data(withJSONObject: dictionary, options: []) else {
+            PrettyPrint.print("Invalid Discord message dictionary", prefixColor: .red)
+            return nil
+        }
+
+        return data
+    }
+
+    /// Upload a file to Discord via webhook.
+    ///
+    /// - Parameters:
+    ///   - data:       The file data to upload.
+    ///   - outputType: The output type of the file to upload.
+    ///   - discord:    The Discord configuration.
+    private static func upload(_ data: Data, of outputType: OutputType, for discord: DiscordConfiguration) async {
+
+        guard let url: URL = URL(string: discord.webhookURL) else {
+            PrettyPrint.print("Invalid Discord webhook URL: \(discord.webhookURL)", prefixColor: .red)
+            return
+        }
+
+        let boundary: String = "\(String.identifier).\(UUID().uuidString)"
+        var request: URLRequest = URLRequest(url: url)
+        request.httpMethod = "POST"
+        request.setValue("multipart/form-data; boundary=\(boundary)", forHTTPHeaderField: "Content-Type")
+        request.httpBody = uploadData(from: data, of: outputType, boundary: boundary)
+
+        PrettyPrint.print("Uploading \(outputType.description) report via Discord")
+
+        do {
+            let (_, response): (Data, URLResponse) = try await URLSession.shared.data(for: request)
+
+            guard let httpResponse: HTTPURLResponse = response as? HTTPURLResponse else {
+                PrettyPrint.print("Unable to get response from Discord webhook URL: \(url)", prefixColor: .red)
+                return
+            }
+
+            guard httpResponse.statusCode == 200 else {
+                let string: String = HTTP.errorMessage(httpResponse.statusCode, for: url)
+                PrettyPrint.print(string, prefixColor: .red)
+                return
+            }
+        } catch {
+            PrettyPrint.print(error.localizedDescription, prefixColor: .red)
+        }
+    }
+
+    /// Generate multipart form data for a Discord file upload.
+    ///
+    /// - Parameters:
+    ///   - data:       The file data to upload.
+    ///   - outputType: The output type of the file to upload.
+    ///   - boundary:   A unique string used as a boundary to separate form parts.
+    /// - Returns: A `Data` object if successful, otherwise `nil`.
+    private static func uploadData(from data: Data, of outputType: OutputType, boundary: String) -> Data? {
+
+        guard let file: String = String(data: data, encoding: .utf8) else {
+            PrettyPrint.print("Invalid report file data", prefixColor: .red)
+            return nil
+        }
+
+        let dateFormatter: DateFormatter = DateFormatter()
+        dateFormatter.dateFormat = "yyyy-MM-dd"
+        let dateString: String = dateFormatter.string(from: Date())
+        let filename: String = "KMART Report \(dateString).\(outputType.fileExtension)"
+
+        var string: String = ""
+        string.append("--\(boundary)\r\n")
+        string.append("Content-Disposition: form-data; name=\"files[0]\"; filename=\"\(filename)\"\r\n")
+        string.append("Content-Type: application/octet-stream\r\n\r\n")
+        string.append(file)
+        string.append("\r\n--\(boundary)--\r\n")
+
+        return string.data(using: .utf8)
+    }
+}
\ No newline at end of file
diff --git a/KMART/Model/Configuration.swift b/KMART/Model/Configuration.swift
index 6107514..75b99f2 100644
--- a/KMART/Model/Configuration.swift
+++ b/KMART/Model/Configuration.swift
@@ -28,6 +28,8 @@ struct Configuration {
     var output: [OutputType: String] = [:]
     /// Slack configuration object.
     var slack: SlackConfiguration = SlackConfiguration([:])
+    /// Discord configuration object.
+    var discord: DiscordConfiguration = DiscordConfiguration([:])
     /// List of endpoints to report on, derived from the requested report types.
     var endpoints: [Endpoint] {
         let endpoints: [Endpoint] = reports.flatMap { $0.endpoints }
@@ -75,7 +77,8 @@ struct Configuration {
         configureReports(dictionary["reports"] as? [String: Bool] ?? [:])
         configureReportOptions(dictionary["reports_options"] as? [String: Int] ?? [:])
         configureOutput(dictionary["output"] as? [String: String] ?? [:])
-        configureSlack(dictionary["slack"] as? [String: Any] ?? [: ])
+        configureSlack(dictionary["slack"] as? [String: Any] ?? [:])
+        configureDiscord(dictionary["discord"] as? [String: Any] ?? [:])
     }
 
     /// Set the default Jamf API configuration.
@@ -175,4 +178,12 @@ struct Configuration {
     private mutating func configureSlack(_ dictionary: [String: Any]) {
         slack = SlackConfiguration(dictionary)
     }
+
+    /// Set the **Discord** configuration.
+    ///
+    /// - Parameters:
+    ///   - dictionary: The dictionary containing the **Discord** configuration options.
+    private mutating func configureDiscord(_ dictionary: [String: Any]) {
+        discord = DiscordConfiguration(dictionary)
+    }
 }
diff --git a/KMART/Model/DiscordConfiguration.swift b/KMART/Model/DiscordConfiguration.swift
new file mode 100644
index 0000000..35a9dc8
--- /dev/null
+++ b/KMART/Model/DiscordConfiguration.swift
@@ -0,0 +1,37 @@
+//
+//  DiscordConfiguration.swift
+//  KMART
+//
+
+import Foundation
+
+/// Struct used to hold Discord configuration.
+struct DiscordConfiguration {
+    /// Default message text.
+    static let defaultText: String = "KMART Report(s) have been uploaded."
+    /// Set to `true` to enable reporting via Discord.
+    var enabled: Bool = false
+    /// Discord webhook URL.
+    var webhookURL: String = ""
+    /// Message text.
+    var text: String = ""
+    /// Discord attachments.
+    var attachments: [OutputType] = []
+
+    /// Initialize a DiscordConfiguration struct by passing in a custom dictionary.
+    ///
+    /// - Parameters:
+    ///   - dictionary: Custom dictionary containing Discord configuration properties.
+    init(_ dictionary: [String: Any] = [:]) {
+        enabled = dictionary["enabled"] as? Bool ?? false
+        webhookURL = dictionary["webhook_url"] as? String ?? ""
+        text = dictionary["text"] as? String ?? DiscordConfiguration.defaultText
+        if let array: [String] = dictionary["attachments"] as? [String] {
+            for item in array {
+                if let attachment: OutputType = OutputType(rawValue: item) {
+                    attachments.append(attachment)
+                }
+            }
+        }
+    }
+}
\ No newline at end of file