diff --git a/ElementX/Sources/Other/Pills/PillAttachmentViewProvider.swift b/ElementX/Sources/Other/Pills/PillAttachmentViewProvider.swift
index 40c174a33..7ad0cb3b6 100644
--- a/ElementX/Sources/Other/Pills/PillAttachmentViewProvider.swift
+++ b/ElementX/Sources/Other/Pills/PillAttachmentViewProvider.swift
@@ -73,6 +73,7 @@ final class PillAttachmentViewProvider: NSTextAttachmentViewProvider {
         // This allows the text view to handle it as a link
         controller.view.isUserInteractionEnabled = false
         self.view = controller.view
+        textAttachment.view = controller.view
         delegate?.registerPillView(controller.view)
     }
 }
diff --git a/ElementX/Sources/Other/Pills/PillConstants.swift b/ElementX/Sources/Other/Pills/PillConstants.swift
index 9dbe25520..fb6e98e5a 100644
--- a/ElementX/Sources/Other/Pills/PillConstants.swift
+++ b/ElementX/Sources/Other/Pills/PillConstants.swift
@@ -24,4 +24,6 @@ enum PillConstants {
 
     /// Used by the WYSIWYG as the urlString value to identify @room mentions
     static let composerAtRoomURLString = "#"
+    
+    static let maxWidth: CGFloat = 235
 }
diff --git a/ElementX/Sources/Other/Pills/PillTextAttachment.swift b/ElementX/Sources/Other/Pills/PillTextAttachment.swift
index a294e1919..42745b1ec 100644
--- a/ElementX/Sources/Other/Pills/PillTextAttachment.swift
+++ b/ElementX/Sources/Other/Pills/PillTextAttachment.swift
@@ -26,6 +26,7 @@ final class PillTextAttachment: NSTextAttachment {
     }
     
     private(set) var pillData: PillTextAttachmentData!
+    weak var view: UIView?
     private var lastBounds: CGRect?
     
     func invalidateLastBounds() {
@@ -33,14 +34,20 @@ final class PillTextAttachment: NSTextAttachment {
     }
     
     override func attachmentBounds(for textContainer: NSTextContainer?, proposedLineFragment lineFrag: CGRect, glyphPosition position: CGPoint, characterIndex charIndex: Int) -> CGRect {
+        var rect: CGRect
         if let lastBounds {
             return lastBounds
+        } else if let view {
+            rect = CGRect(origin: .zero, size: view.sizeThatFits(UIView.layoutFittingExpandedSize))
+        } else {
+            rect = super.attachmentBounds(for: textContainer, proposedLineFragment: lineFrag, glyphPosition: position, characterIndex: charIndex)
         }
-        var rect = super.attachmentBounds(for: textContainer, proposedLineFragment: lineFrag, glyphPosition: position, characterIndex: charIndex)
         
         let fontData = pillData.fontData
         // Align the pill text vertically with the surrounding text.
         rect.origin.y = fontData.descender + (fontData.lineHeight - rect.height) / 2.0
+        // Set the max width of the pill
+        rect.size.width = min(rect.size.width, PillConstants.maxWidth)
         lastBounds = rect
         return rect
     }
diff --git a/ElementX/Sources/Other/Pills/PillView.swift b/ElementX/Sources/Other/Pills/PillView.swift
index aa597d183..3d7509355 100644
--- a/ElementX/Sources/Other/Pills/PillView.swift
+++ b/ElementX/Sources/Other/Pills/PillView.swift
@@ -34,7 +34,6 @@ struct PillView: View {
         .padding(.vertical, 4)
         // for now design has defined no color so we will just use gray
         .background(Capsule().foregroundColor(context.viewState.isOwnMention ? .compound.bgCriticalPrimary : .gray))
-        .frame(maxWidth: 235)
         .onChange(of: context.viewState.displayText) { _ in
             didChangeText()
         }
@@ -53,9 +52,13 @@ struct PillView_Previews: PreviewProvider, TestablePreview {
             .previewDisplayName("Loading Own")
         PillView(imageProvider: mockMediaProvider,
                  context: PillContext.mock(type: .loadedUser(isOwn: false))) { }
+            // To simulate the trimming that happens at UIKit level
+            .frame(maxWidth: PillConstants.maxWidth)
             .previewDisplayName("Loaded Long")
         PillView(imageProvider: mockMediaProvider,
                  context: PillContext.mock(type: .loadedUser(isOwn: true))) { }
+            // To simulate the trimming that happens at UIKit level
+            .frame(maxWidth: PillConstants.maxWidth)
             .previewDisplayName("Loaded Long Own")
         PillView(imageProvider: mockMediaProvider,
                  context: PillContext.mock(type: .allUsers)) { }