diff --git a/internal/tui/components/chat/sidebar/sidebar.go b/internal/tui/components/chat/sidebar/sidebar.go
index edec996e32558fadb6112ef9781a26413182a06a..eeabeac3f9a7b1f17c2b24acc4950deb186ff56b 100644
--- a/internal/tui/components/chat/sidebar/sidebar.go
+++ b/internal/tui/components/chat/sidebar/sidebar.go
@@ -12,6 +12,7 @@ import (
 	"github.com/charmbracelet/crush/internal/config"
 	"github.com/charmbracelet/crush/internal/csync"
 	"github.com/charmbracelet/crush/internal/diff"
+	"github.com/charmbracelet/crush/internal/fsext"
 	"github.com/charmbracelet/crush/internal/history"
 	"github.com/charmbracelet/crush/internal/lsp"
 	"github.com/charmbracelet/crush/internal/pubsub"
@@ -190,8 +191,8 @@ func (m *sidebarCmp) handleFileHistoryEvent(event pubsub.Event[history.File]) te
 				// If the version is not greater than the latest, we ignore it
 				continue
 			}
-			before := existing.History.initialVersion.Content
-			after := existing.History.latestVersion.Content
+			before, _ := fsext.ToUnixLineEndings(existing.History.initialVersion.Content)
+			after, _ := fsext.ToUnixLineEndings(existing.History.latestVersion.Content)
 			path := existing.History.initialVersion.Path
 			cwd := config.Get().WorkingDir()
 			path = strings.TrimPrefix(path, cwd)
@@ -248,7 +249,9 @@ func (m *sidebarCmp) loadSessionFiles() tea.Msg {
 	for path, fh := range fileMap {
 		cwd := config.Get().WorkingDir()
 		path = strings.TrimPrefix(path, cwd)
-		_, additions, deletions := diff.GenerateDiff(fh.initialVersion.Content, fh.latestVersion.Content, path)
+		before, _ := fsext.ToUnixLineEndings(fh.initialVersion.Content)
+		after, _ := fsext.ToUnixLineEndings(fh.latestVersion.Content)
+		_, additions, deletions := diff.GenerateDiff(before, after, path)
 		sessionFiles = append(sessionFiles, SessionFile{
 			History:   fh,
 			FilePath:  path,