diff --git a/Documentation/SwiftlyDocs.docc/swiftly-cli-reference.md b/Documentation/SwiftlyDocs.docc/swiftly-cli-reference.md
index 8a667e17..4f4137a6 100644
--- a/Documentation/SwiftlyDocs.docc/swiftly-cli-reference.md
+++ b/Documentation/SwiftlyDocs.docc/swiftly-cli-reference.md
@@ -405,7 +405,7 @@ written to this file as commands that can be run after the installation.
 Perform swiftly initialization into your user account.
 
 ```
-swiftly init [--no-modify-profile] [--overwrite] [--platform=<platform>] [--skip-install] [--quiet-shell-followup] [--assume-yes] [--verbose] [--version] [--help]
+swiftly init [--no-modify-profile] [--overwrite] [--platform=<platform>] [--skip-install] [--quiet-shell-followup] [--sudo-install-packages] [--assume-yes] [--verbose] [--version] [--help]
 ```
 
 **--no-modify-profile:**
@@ -433,6 +433,11 @@ swiftly init [--no-modify-profile] [--overwrite] [--platform=<platform>] [--skip
 *Quiet shell follow up commands*
 
 
+**--sudo-install-packages:**
+
+*Run sudo if there are post-installation packages to install (Linux only)*
+
+
 **--assume-yes:**
 
 *Disable confirmation prompts by assuming 'yes'*
diff --git a/Sources/Swiftly/Init.swift b/Sources/Swiftly/Init.swift
index bc071334..ecd7050d 100644
--- a/Sources/Swiftly/Init.swift
+++ b/Sources/Swiftly/Init.swift
@@ -20,21 +20,25 @@ internal struct Init: SwiftlyCommand {
     var skipInstall: Bool = false
     @Flag(help: "Quiet shell follow up commands")
     var quietShellFollowup: Bool = false
+    @Flag(help: "Run sudo if there are post-installation packages to install (Linux only)")
+    var sudoInstallPackages: Bool = false
 
     @OptionGroup var root: GlobalOptions
 
+    internal static var allowedInstallCommands: Regex<(Substring, Substring, Substring)> { try! Regex("^(apt-get|yum) -y install( [A-Za-z0-9:\\-\\+]+)+$") }
+
     private enum CodingKeys: String, CodingKey {
-        case noModifyProfile, overwrite, platform, skipInstall, root, quietShellFollowup
+        case noModifyProfile, overwrite, platform, skipInstall, root, quietShellFollowup, sudoInstallPackages
     }
 
     public mutating func validate() throws {}
 
     internal mutating func run() async throws {
-        try await Self.execute(assumeYes: self.root.assumeYes, noModifyProfile: self.noModifyProfile, overwrite: self.overwrite, platform: self.platform, verbose: self.root.verbose, skipInstall: self.skipInstall, quietShellFollowup: self.quietShellFollowup)
+        try await Self.execute(assumeYes: self.root.assumeYes, noModifyProfile: self.noModifyProfile, overwrite: self.overwrite, platform: self.platform, verbose: self.root.verbose, skipInstall: self.skipInstall, quietShellFollowup: self.quietShellFollowup, sudoInstallPackages: self.sudoInstallPackages)
     }
 
     /// Initialize the installation of swiftly.
-    internal static func execute(assumeYes: Bool, noModifyProfile: Bool, overwrite: Bool, platform: String?, verbose: Bool, skipInstall: Bool, quietShellFollowup: Bool) async throws {
+    internal static func execute(assumeYes: Bool, noModifyProfile: Bool, overwrite: Bool, platform: String?, verbose: Bool, skipInstall: Bool, quietShellFollowup: Bool, sudoInstallPackages: Bool) async throws {
         try Swiftly.currentPlatform.verifySwiftlySystemPrerequisites()
 
         var config = try? Config.load()
@@ -290,6 +294,12 @@ internal struct Init: SwiftlyCommand {
         }
 
         if let postInstall {
+#if !os(Linux)
+            if sudoInstallPackages {
+                SwiftlyCore.print("Sudo installing missing packages has no effect on non-Linux platforms.")
+            }
+#endif
+
             SwiftlyCore.print("""
             There are some dependencies that should be installed before using this toolchain.
             You can run the following script as the system administrator (e.g. root) to prepare
@@ -298,6 +308,42 @@ internal struct Init: SwiftlyCommand {
                 \(postInstall)
 
             """)
+
+            if sudoInstallPackages {
+                // This is very security sensitive code here and that's why there's special process handling
+                // and an allow-list of what we will attempt to run as root. Also, the sudo binary is run directly
+                // with a fully-qualified path without any checking in order to avoid TOCTOU.
+
+                guard try Self.allowedInstallCommands.wholeMatch(in: postInstall) != nil else {
+                    fatalError("post installation command \(postInstall) does not match allowed patterns for sudo")
+                }
+
+                let p = Process()
+                p.executableURL = URL(fileURLWithPath: "/usr/bin/sudo")
+                p.arguments = ["-k"] + ["-p", "Enter your sudo password to run it right away (Ctrl-C aborts): "] + postInstall.split(separator: " ").map { String($0) }
+
+                do {
+                    try p.run()
+
+                    // Attach this process to our process group so that Ctrl-C and other signals work
+                    let pgid = tcgetpgrp(STDOUT_FILENO)
+                    if pgid != -1 {
+                        tcsetpgrp(STDOUT_FILENO, p.processIdentifier)
+                    }
+
+                    defer { if pgid != -1 {
+                        tcsetpgrp(STDOUT_FILENO, pgid)
+                    }}
+
+                    p.waitUntilExit()
+
+                    if p.terminationStatus == 0 {
+                        SwiftlyCore.print("sudo could not be run to install the packages")
+                    }
+                } catch {
+                    SwiftlyCore.print("sudo could not be run to install the packages")
+                }
+            }
         }
     }
 }
diff --git a/Sources/Swiftly/Proxy.swift b/Sources/Swiftly/Proxy.swift
index d0640ee4..ce14ce74 100644
--- a/Sources/Swiftly/Proxy.swift
+++ b/Sources/Swiftly/Proxy.swift
@@ -24,8 +24,8 @@ public enum Proxy {
 
                     if CommandLine.arguments.count == 1 {
                         // User ran swiftly with no extra arguments in an uninstalled environment, so we jump directly into
-                        //  an simple init.
-                        try await Init.execute(assumeYes: false, noModifyProfile: false, overwrite: false, platform: nil, verbose: false, skipInstall: false, quietShellFollowup: false)
+                        //  a simple init.
+                        try await Init.execute(assumeYes: false, noModifyProfile: false, overwrite: false, platform: nil, verbose: false, skipInstall: false, quietShellFollowup: false, sudoInstallPackages: false)
                         return
                     } else if CommandLine.arguments.count >= 2 && CommandLine.arguments[1] == "init" {
                         // Let the user run the init command with their arguments, if any.
diff --git a/Tests/SwiftlyTests/InitTests.swift b/Tests/SwiftlyTests/InitTests.swift
index c4169d99..bfde22c4 100644
--- a/Tests/SwiftlyTests/InitTests.swift
+++ b/Tests/SwiftlyTests/InitTests.swift
@@ -125,4 +125,15 @@ final class InitTests: SwiftlyTests {
             XCTAssertTrue(Swiftly.currentPlatform.swiftlyToolchainsDir.appendingPathComponent("foo.txt").fileExists())
         }
     }
+
+    func testAllowedInstalledCommands() async throws {
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "apt-get -y install python3 libsqlite3") != nil)
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "yum -y install python3 libsqlite3") != nil)
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "yum -y install python3 libsqlite3-dev") != nil)
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "yum -y install libstdc++-dev:i386") != nil)
+
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "SOME_ENV_VAR=abcde yum -y install libstdc++-dev:i386") == nil)
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "apt-get -y install libstdc++-dev:i386; rm -rf /") == nil)
+        XCTAssertTrue(try Init.allowedInstallCommands.wholeMatch(in: "apt-get -y install libstdc++-dev:i386\nrm -rf /") == nil)
+    }
 }