diff --git a/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarComponent.swift b/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarComponent.swift
index 130fc6098..c6663721b 100644
--- a/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarComponent.swift
+++ b/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarComponent.swift
@@ -26,16 +26,19 @@ struct EditorJumpBarComponent: View {
     @State var selection: CEWorkspaceFile
     @State var isHovering: Bool = false
     @State var button = NSPopUpButton()
+    @Binding var truncatedCrumbWidth: CGFloat?
 
     init(
         fileItem: CEWorkspaceFile,
         tappedOpenFile: @escaping (CEWorkspaceFile) -> Void,
-        isLastItem: Bool
+        isLastItem: Bool,
+        isTruncated: Binding<CGFloat?>
     ) {
         self.fileItem = fileItem
         self._selection = .init(wrappedValue: fileItem)
         self.tappedOpenFile = tappedOpenFile
         self.isLastItem = isLastItem
+        self._truncatedCrumbWidth = isTruncated
     }
 
     var siblings: [CEWorkspaceFile] {
@@ -65,6 +68,28 @@ struct EditorJumpBarComponent: View {
 
             return button
         }
+        .frame(
+            maxWidth: isHovering || isLastItem ? nil : truncatedCrumbWidth,
+            alignment: .leading
+        )
+        .mask(
+            LinearGradient(
+                gradient: Gradient(
+                    stops: truncatedCrumbWidth == nil ?
+                    [
+                        .init(color: .black, location: 0),
+                        .init(color: .black, location: 1)
+                    ] : [
+                        .init(color: .black, location: 0),
+                        .init(color: .black, location: 0.8),
+                        .init(color: .clear, location: 1)
+                    ]
+                ),
+                startPoint: .leading,
+                endPoint: .trailing
+            )
+        )
+        .clipped()
         .padding(.trailing, 11)
         .background {
             Color(nsColor: colorScheme == .dark ? .white : .black)
@@ -83,7 +108,9 @@ struct EditorJumpBarComponent: View {
         }
         .padding(.vertical, 3)
         .onHover { hover in
-            isHovering = hover
+            withAnimation(.easeInOut(duration: 0.2)) {
+                isHovering = hover
+            }
         }
         .onLongPressGesture(minimumDuration: 0) {
             button.performClick(nil)
diff --git a/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarView.swift b/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarView.swift
index ce53d07b8..5c70aef98 100644
--- a/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarView.swift
+++ b/CodeEdit/Features/Editor/JumpBar/Views/EditorJumpBarView.swift
@@ -25,6 +25,12 @@ struct EditorJumpBarView: View {
 
     static let height = 28.0
 
+    @State private var textWidth: CGFloat = 0
+    @State private var containerWidth: CGFloat = 0
+    @State private var isTruncated: Bool = false
+    @State private var crumbWidth: CGFloat?
+    @State private var firstCrumbWidth: CGFloat?
+
     init(
         file: CEWorkspaceFile?,
         shouldShowTabBar: Bool,
@@ -50,25 +56,60 @@ struct EditorJumpBarView: View {
     }
 
     var body: some View {
-        ScrollView(.horizontal, showsIndicators: false) {
-            HStack(spacing: 0) {
-                if file == nil {
-                    Text("No Selection")
-                        .font(.system(size: 11, weight: .regular))
-                        .foregroundColor(
-                            activeState != .inactive
-                            ? isActiveEditor ? .primary : .secondary
-                            : Color(nsColor: .tertiaryLabelColor)
-                        )
-                } else {
-                    ForEach(fileItems, id: \.self) { fileItem in
-                        EditorJumpBarComponent(
-                            fileItem: fileItem,
-                            tappedOpenFile: tappedOpenFile,
-                            isLastItem: fileItems.last == fileItem
-                        )
+        GeometryReader { containerProxy in
+            ScrollView(.horizontal, showsIndicators: false) {
+                HStack(spacing: 0) {
+                    if file == nil {
+                        Text("No Selection")
+                            .font(.system(size: 11, weight: .regular))
+                            .foregroundColor(
+                                activeState != .inactive
+                                ? isActiveEditor ? .primary : .secondary
+                                : Color(nsColor: .tertiaryLabelColor)
+                            )
+                    } else {
+                        ForEach(fileItems, id: \.self) { fileItem in
+                            EditorJumpBarComponent(
+                                fileItem: fileItem,
+                                tappedOpenFile: tappedOpenFile,
+                                isLastItem: fileItems.last == fileItem,
+                                isTruncated: fileItems.first == fileItem ? $firstCrumbWidth : $crumbWidth
+                            )
+                        }
+
                     }
                 }
+                .background(
+                    GeometryReader { proxy in
+                        Color.clear
+                            .onAppear {
+                                if crumbWidth == nil {
+                                    textWidth = proxy.size.width
+                                }
+                            }
+                            .onChange(of: proxy.size.width) { newValue in
+                                if crumbWidth == nil {
+                                    textWidth = newValue
+                                }
+                            }
+                    }
+                )
+            }
+            .onAppear {
+                containerWidth = containerProxy.size.width
+            }
+            .onChange(of: containerProxy.size.width) { newValue in
+                containerWidth = newValue
+            }
+            .onChange(of: textWidth) { _ in
+                withAnimation(.easeInOut(duration: 0.2)) {
+                    resize()
+                }
+            }
+            .onChange(of: containerWidth) { _ in
+                withAnimation(.easeInOut(duration: 0.2)) {
+                    resize()
+                }
             }
         }
         .padding(.horizontal, shouldShowTabBar ? (file == nil ? 10 : 4) : 0)
@@ -86,4 +127,40 @@ struct EditorJumpBarView: View {
         .opacity(activeState == .inactive ? 0.8 : 1.0)
         .grayscale(isActiveEditor ? 0.0 : 1.0)
     }
+
+    private func resize() {
+        let minWidth: CGFloat = 20
+        let snapThreshold: CGFloat = 30
+        let maxWidth: CGFloat = textWidth / CGFloat(fileItems.count)
+        let exponent: CGFloat = 5.0
+        var betweenWidth: CGFloat = 0.0
+
+        if textWidth >= containerWidth {
+            let scale = max(0, min(1, containerWidth / textWidth))
+            betweenWidth = floor((minWidth + (maxWidth - minWidth) * pow(scale, exponent)))
+            if betweenWidth < snapThreshold {
+                betweenWidth = minWidth
+            }
+            crumbWidth = betweenWidth
+        } else {
+            crumbWidth = nil
+        }
+
+        if betweenWidth > snapThreshold {
+            firstCrumbWidth = nil
+        } else {
+            let otherCrumbs = CGFloat(max(fileItems.count - 1, 1))
+            let usedWidth = otherCrumbs * snapThreshold
+
+            // Multiplier to reserve extra space for other crumbs in the jump bar.
+            // Increasing this value causes the first crumb to truncate sooner.
+            let crumbSpacingMultiplier: CGFloat = 1.5
+            let availableForFirst = containerWidth - usedWidth * crumbSpacingMultiplier
+            if availableForFirst < snapThreshold {
+                firstCrumbWidth = minWidth
+            } else {
+                firstCrumbWidth = availableForFirst
+            }
+        }
+    }
 }