diff --git a/CHANGELOG.md b/CHANGELOG.md
index 93ca8eca..1e7f40d8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,11 @@
 
 All notable changes to cmuxterm are documented here.
 
+## [1.19.4] - 2026-02-09
+
+### Fixed
+- Update pill never appearing due to constraint/sizing feedback loop
+
 ## [1.19.3] - 2026-02-09
 
 ### Fixed
diff --git a/GhosttyTabs.xcodeproj/project.pbxproj b/GhosttyTabs.xcodeproj/project.pbxproj
index e0116a27..af21702e 100644
--- a/GhosttyTabs.xcodeproj/project.pbxproj
+++ b/GhosttyTabs.xcodeproj/project.pbxproj
@@ -538,7 +538,7 @@
 				CODE_SIGN_ENTITLEMENTS = "";
 				CODE_SIGN_STYLE = Automatic;
 				COMBINE_HIDPI_IMAGES = YES;
-				CURRENT_PROJECT_VERSION = 28;
+				CURRENT_PROJECT_VERSION = 29;
 				DEVELOPMENT_TEAM = "";
 				ENABLE_HARDENED_RUNTIME = NO;
 				GENERATE_INFOPLIST_FILE = YES;
@@ -554,7 +554,7 @@
 					"$(inherited)",
 					"@executable_path/../Frameworks",
 				);
-				MARKETING_VERSION = 1.19.3;
+				MARKETING_VERSION = 1.19.4;
 				OTHER_LDFLAGS = (
 					"-lc++",
 					"-framework",
@@ -583,7 +583,7 @@
 				CODE_SIGN_ENTITLEMENTS = "";
 				CODE_SIGN_STYLE = Automatic;
 				COMBINE_HIDPI_IMAGES = YES;
-				CURRENT_PROJECT_VERSION = 28;
+				CURRENT_PROJECT_VERSION = 29;
 				DEVELOPMENT_TEAM = "";
 				ENABLE_HARDENED_RUNTIME = NO;
 				GENERATE_INFOPLIST_FILE = YES;
@@ -599,7 +599,7 @@
 					"$(inherited)",
 					"@executable_path/../Frameworks",
 				);
-				MARKETING_VERSION = 1.19.3;
+				MARKETING_VERSION = 1.19.4;
 				OTHER_LDFLAGS = (
 					"-lc++",
 					"-framework",
@@ -652,10 +652,10 @@
 			isa = XCBuildConfiguration;
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
-				CURRENT_PROJECT_VERSION = 28;
+				CURRENT_PROJECT_VERSION = 29;
 				GENERATE_INFOPLIST_FILE = YES;
 				MACOSX_DEPLOYMENT_TARGET = 13.0;
-				MARKETING_VERSION = 1.19.3;
+				MARKETING_VERSION = 1.19.4;
 				ONLY_ACTIVE_ARCH = YES;
 				PRODUCT_BUNDLE_IDENTIFIER = com.cmuxterm.appuitests;
 				PRODUCT_NAME = "$(TARGET_NAME)";
@@ -669,10 +669,10 @@
 			isa = XCBuildConfiguration;
 			buildSettings = {
 				CODE_SIGN_STYLE = Automatic;
-				CURRENT_PROJECT_VERSION = 28;
+				CURRENT_PROJECT_VERSION = 29;
 				GENERATE_INFOPLIST_FILE = YES;
 				MACOSX_DEPLOYMENT_TARGET = 13.0;
-				MARKETING_VERSION = 1.19.3;
+				MARKETING_VERSION = 1.19.4;
 				ONLY_ACTIVE_ARCH = YES;
 				PRODUCT_BUNDLE_IDENTIFIER = com.cmuxterm.appuitests;
 				PRODUCT_NAME = "$(TARGET_NAME)";
diff --git a/Sources/Update/UpdatePill.swift b/Sources/Update/UpdatePill.swift
index ace5eb9b..a3ef524a 100644
--- a/Sources/Update/UpdatePill.swift
+++ b/Sources/Update/UpdatePill.swift
@@ -21,8 +21,6 @@ struct UpdatePill: View {
                 UpdatePopoverView(model: model)
             }
             .opacity(visible ? 1 : 0)
-            .frame(width: visible ? nil : 0, height: visible ? nil : 0)
-            .clipped()
     }
 
     @ViewBuilder
diff --git a/Sources/WindowToolbarController.swift b/Sources/WindowToolbarController.swift
index c340ce88..dd7e5cc3 100644
--- a/Sources/WindowToolbarController.swift
+++ b/Sources/WindowToolbarController.swift
@@ -128,16 +128,17 @@ final class WindowToolbarController: NSObject, NSToolbarDelegate {
             let view = NonDraggableHostingView(rootView: UpdatePill(model: updateViewModel))
             let key = ObjectIdentifier(toolbar)
             item.view = view
-            sizeToolbarItem(for: key, hostingView: view)
+            let visible = !updateViewModel.effectiveState.isIdle
+            sizeToolbarItem(for: key, hostingView: view, visible: visible)
             updateSizeCancellables[key]?.cancel()
             updateSizeCancellables[key] = updateViewModel.$state
                 .receive(on: DispatchQueue.main)
-                .sink { [weak self, weak view] _ in
+                .sink { [weak self, weak view] newState in
                     // @Published fires on willSet, so SwiftUI hasn't processed the
                     // new state yet. Defer measurement to the next run loop cycle.
                     DispatchQueue.main.async { [weak self, weak view] in
                         guard let self, let view else { return }
-                        self.sizeToolbarItem(for: key, hostingView: view)
+                        self.sizeToolbarItem(for: key, hostingView: view, visible: !newState.isIdle)
                     }
                 }
             return item
@@ -146,10 +147,19 @@ final class WindowToolbarController: NSObject, NSToolbarDelegate {
         return nil
     }
 
-    private func sizeToolbarItem(for key: ObjectIdentifier, hostingView: NSView) {
+    private func sizeToolbarItem(for key: ObjectIdentifier, hostingView: NSView, visible: Bool) {
+        // Deactivate existing constraints before measuring so they don't
+        // clamp fittingSize to zero (chicken-and-egg sizing problem).
+        if let constraints = updateViewConstraints[key] {
+            constraints.width.isActive = false
+            constraints.height.isActive = false
+        }
+
         hostingView.invalidateIntrinsicContentSize()
         hostingView.layoutSubtreeIfNeeded()
-        let size = hostingView.fittingSize
+        let naturalSize = hostingView.fittingSize
+        let size = visible ? naturalSize : .zero
+
         hostingView.setFrameSize(size)
         hostingView.setContentHuggingPriority(.required, for: .horizontal)
         hostingView.setContentHuggingPriority(.required, for: .vertical)
@@ -157,6 +167,8 @@ final class WindowToolbarController: NSObject, NSToolbarDelegate {
         if let constraints = updateViewConstraints[key] {
             constraints.width.constant = size.width
             constraints.height.constant = size.height
+            constraints.width.isActive = true
+            constraints.height.isActive = true
         } else {
             let width = hostingView.widthAnchor.constraint(equalToConstant: size.width)
             let height = hostingView.heightAnchor.constraint(equalToConstant: size.height)
diff --git a/docs-site/content/docs/changelog.mdx b/docs-site/content/docs/changelog.mdx
index 3e575faa..c74f5ade 100644
--- a/docs-site/content/docs/changelog.mdx
+++ b/docs-site/content/docs/changelog.mdx
@@ -5,6 +5,11 @@ description: Release notes and version history for cmuxterm
 
 All notable changes to cmuxterm are documented here.
 
+## [1.19.4] - 2026-02-09
+
+### Fixed
+- Update pill never appearing due to constraint/sizing feedback loop
+
 ## [1.19.3] - 2026-02-09
 
 ### Fixed