diff --git a/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs b/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
index 0a7a26153a..679a42b394 100644
--- a/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
+++ b/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
@@ -444,7 +444,7 @@ namespace Tgstation.Server.Host.Components.Deployment
 
 				await Task.WhenAll(symATask, symBTask).ConfigureAwait(false);
 
-				await chatManager.SendUpdateMessage(String.Format(CultureInfo.InvariantCulture, "Deployment complete!{0}", watchdog.Running ? " Changes will be applied on next server reboot." : String.Empty), cancellationToken).ConfigureAwait(false);
+				await chatManager.SendUpdateMessage(String.Format(CultureInfo.InvariantCulture, "Deployment complete! Changes will be applied {0}.", watchdog.DeploymentApplicationTime), cancellationToken).ConfigureAwait(false);
 
 				logger.LogDebug("Compile complete!");
 			}
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs b/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
index 1b8e579d40..8eacde8b8c 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
@@ -25,6 +25,9 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		/// <inheritdoc />
 		public sealed override Models.CompileJob ActiveCompileJob => Server?.Dmb.CompileJob;
 
+		/// <inheritdoc />
+		protected override string DeploymentTimeWhileRunning => "immediately";
+
 		/// <inheritdoc />
 		public sealed override RebootState? RebootState => Server?.RebootState;
 
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/ExperimentalWatchdog.cs b/src/Tgstation.Server.Host/Components/Watchdog/ExperimentalWatchdog.cs
index 333582ed73..dc3e4eb1f5 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/ExperimentalWatchdog.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/ExperimentalWatchdog.cs
@@ -34,6 +34,9 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		/// <inheritdoc />
 		public override RebootState? RebootState => Running ? (AlphaIsActive ? alphaServer?.RebootState : bravoServer?.RebootState) : null;
 
+		/// <inheritdoc />
+		protected override string DeploymentTimeWhileRunning => "when DreamDaemon reboots";
+
 		/// <summary>
 		/// Server designation alpha
 		/// </summary>
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/IWatchdog.cs b/src/Tgstation.Server.Host/Components/Watchdog/IWatchdog.cs
index 926d5239ba..8fac965b1f 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/IWatchdog.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/IWatchdog.cs
@@ -21,6 +21,11 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		/// </summary>
 		bool AlphaIsActive { get; }
 
+		/// <summary>
+		/// When new <see cref="Models.CompileJob"/>s will be made active.
+		/// </summary>
+		string DeploymentApplicationTime { get; }
+
 		/// <summary>
 		/// The <see cref="CompileJob"/> currently running on the server
 		/// </summary>
@@ -37,7 +42,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		DreamDaemonLaunchParameters LastLaunchParameters { get; }
 
 		/// <summary>
-		/// The <see cref="Components.Watchdog.RebootState"/> of the active server
+		/// The <see cref="Watchdog.RebootState"/> of the active server
 		/// </summary>
 		RebootState? RebootState { get; }
 
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs b/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
index b3877611ec..3262a914a6 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
@@ -32,6 +32,9 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		/// <inheritdoc />
 		public abstract bool AlphaIsActive { get; }
 
+		/// <inheritdoc />
+		public string DeploymentApplicationTime => Running ? DeploymentTimeWhileRunning : "when DreamDaemon is launched";
+
 		/// <inheritdoc />
 		public abstract Models.CompileJob ActiveCompileJob { get; }
 
@@ -44,6 +47,11 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		/// <inheritdoc />
 		public abstract RebootState? RebootState { get; }
 
+		/// <summary>
+		/// When deployments happen if the <see cref="IWatchdog"/> is <see cref="Running"/>.
+		/// </summary>
+		protected abstract string DeploymentTimeWhileRunning { get; }
+
 		/// <summary>
 		/// <see cref="TaskCompletionSource{TResult}"/> that completes when <see cref="ActiveLaunchParameters"/> are changed and we are <see cref="Running"/>.
 		/// </summary>
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/WindowsWatchdog.cs b/src/Tgstation.Server.Host/Components/Watchdog/WindowsWatchdog.cs
index 74b6b25dac..a1d56b5e59 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/WindowsWatchdog.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/WindowsWatchdog.cs
@@ -19,6 +19,9 @@ namespace Tgstation.Server.Host.Components.Watchdog
 	/// </summary>
 	sealed class WindowsWatchdog : BasicWatchdog
 	{
+		/// <inheritdoc />
+		protected override string DeploymentTimeWhileRunning => "when DreamDaemon reboots";
+
 		/// <summary>
 		/// The <see cref="IIOManager"/> for the <see cref="WindowsWatchdog"/>.
 		/// </summary>