diff --git a/session/session.go b/session/session.go
index 5c8cf88..aa0963e 100644
--- a/session/session.go
+++ b/session/session.go
@@ -368,6 +368,9 @@ func mergeEntrySet(base, local, latest []vault.Entry) []vault.Entry {
 	for id, current := range localByID {
 		original, hadBase := baseByID[id]
 		if !hadBase || !entriesEqual(original, current) {
+			if latestCurrent, latestChanged := latestByID[id]; hadBase && latestChanged && !entriesEqual(original, latestCurrent) && !entriesEqual(latestCurrent, current) {
+				current = mergeConflictedEntry(current, latestCurrent)
+			}
 			latestByID[id] = current
 		}
 	}
@@ -395,6 +398,24 @@ func mergeEntrySet(base, local, latest []vault.Entry) []vault.Entry {
 	return out
 }
 
+func mergeConflictedEntry(current, latest vault.Entry) vault.Entry {
+	displaced := cloneEntry(latest)
+	if sameEntryVersion(current, displaced) {
+		return current
+	}
+
+	mergedHistory := make([]vault.Entry, 0, len(current.History)+1)
+	mergedHistory = append(mergedHistory, displaced)
+	for _, item := range current.History {
+		if sameEntryVersion(item, displaced) {
+			continue
+		}
+		mergedHistory = append(mergedHistory, cloneEntry(item))
+	}
+	current.History = mergedHistory
+	return current
+}
+
 func mapEntries(entries []vault.Entry) map[string]vault.Entry {
 	out := make(map[string]vault.Entry, len(entries))
 	for _, item := range entries {
@@ -429,6 +450,42 @@ func equalAttachments(a, b map[string][]byte) bool {
 	return true
 }
 
+func cloneEntry(entry vault.Entry) vault.Entry {
+	entry.Tags = slices.Clone(entry.Tags)
+	entry.Path = slices.Clone(entry.Path)
+	entry.History = cloneHistory(entry.History)
+	if entry.Fields != nil {
+		fields := make(map[string]string, len(entry.Fields))
+		for key, value := range entry.Fields {
+			fields[key] = value
+		}
+		entry.Fields = fields
+	}
+	if entry.Attachments != nil {
+		attachments := make(map[string][]byte, len(entry.Attachments))
+		for key, value := range entry.Attachments {
+			attachments[key] = slices.Clone(value)
+		}
+		entry.Attachments = attachments
+	}
+	return entry
+}
+
+func cloneHistory(history []vault.Entry) []vault.Entry {
+	if len(history) == 0 {
+		return nil
+	}
+	out := make([]vault.Entry, len(history))
+	for i := range history {
+		out[i] = cloneEntry(history[i])
+	}
+	return out
+}
+
+func sameEntryVersion(a, b vault.Entry) bool {
+	return entriesEqual(a, b)
+}
+
 func mergeGroups(base, local, latest [][]string) [][]string {
 	set := map[string][]string{}
 	for _, path := range latest {
diff --git a/session/session_test.go b/session/session_test.go
index 748c009..91692b2 100644
--- a/session/session_test.go
+++ b/session/session_test.go
@@ -666,3 +666,127 @@ func TestRemoteSaveAndReopenPreservesCrossFeatureState(t *testing.T) {
 		t.Fatalf("RecycleBin after remote reopen = %#v, want retired entry in Root/Archive", current.RecycleBin)
 	}
 }
+
+func TestSynchronizeRemotePreservesOverwrittenRemoteVariantInHistory(t *testing.T) {
+	t.Parallel()
+
+	key := vault.MasterKey{Password: "correct horse battery staple"}
+	model := vault.Model{
+		Entries: []vault.Entry{
+			{
+				ID:       "entry-1",
+				Title:    "Vault Console",
+				Username: "dannyocean",
+				Password: "token-1",
+				URL:      "https://vault.crew.example.invalid",
+				Path:     []string{"Root", "Internet"},
+			},
+		},
+	}
+
+	var remoteBytes bytes.Buffer
+	if err := vault.SaveKDBXWithKey(&remoteBytes, model, key); err != nil {
+		t.Fatalf("SaveKDBXWithKey(seed remote) error = %v", err)
+	}
+
+	etag := "\"v1\""
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		switch r.Method {
+		case http.MethodGet:
+			w.Header().Set("ETag", etag)
+			_, _ = w.Write(remoteBytes.Bytes())
+		case http.MethodPut:
+			if got := r.Header.Get("If-Match"); got != etag {
+				t.Fatalf("If-Match header = %q, want %q", got, etag)
+			}
+			payload, err := io.ReadAll(r.Body)
+			if err != nil {
+				t.Fatalf("ReadAll(PUT body) error = %v", err)
+			}
+			remoteBytes.Reset()
+			if _, err := remoteBytes.Write(payload); err != nil {
+				t.Fatalf("Write(remoteBytes) error = %v", err)
+			}
+			switch etag {
+			case "\"v1\"":
+				etag = "\"v2\""
+			default:
+				etag = "\"v3\""
+			}
+			w.Header().Set("ETag", etag)
+			w.WriteHeader(http.StatusNoContent)
+		default:
+			t.Fatalf("unexpected method %s", r.Method)
+		}
+	}))
+	defer server.Close()
+
+	client := webdav.Client{BaseURL: server.URL}
+
+	var first Manager
+	if err := first.OpenRemote(client, "vaults/main.kdbx", key); err != nil {
+		t.Fatalf("first OpenRemote() error = %v", err)
+	}
+	var second Manager
+	if err := second.OpenRemote(client, "vaults/main.kdbx", key); err != nil {
+		t.Fatalf("second OpenRemote() error = %v", err)
+	}
+
+	firstCurrent, err := first.Current()
+	if err != nil {
+		t.Fatalf("first Current() error = %v", err)
+	}
+	firstCurrent.UpsertEntry(vault.Entry{
+		ID:       "entry-1",
+		Title:    "Vault Console",
+		Username: "dannyocean",
+		Password: "remote-token-2",
+		URL:      "https://vault.crew.example.invalid",
+		Notes:    "updated remotely first",
+		Path:     []string{"Root", "Internet"},
+	})
+	first.Replace(firstCurrent)
+	if err := first.SaveRemote(); err != nil {
+		t.Fatalf("first SaveRemote() error = %v", err)
+	}
+
+	secondCurrent, err := second.Current()
+	if err != nil {
+		t.Fatalf("second Current() error = %v", err)
+	}
+	secondCurrent.UpsertEntry(vault.Entry{
+		ID:       "entry-1",
+		Title:    "Vault Console",
+		Username: "dannyocean",
+		Password: "local-token-2",
+		URL:      "https://vault.crew.example.invalid/security/badges",
+		Path:     []string{"Root", "Internet"},
+	})
+	second.Replace(secondCurrent)
+	if err := second.Synchronize(); err != nil {
+		t.Fatalf("second Synchronize() error = %v", err)
+	}
+
+	var reopened Manager
+	if err := reopened.OpenRemote(client, "vaults/main.kdbx", key); err != nil {
+		t.Fatalf("reopened OpenRemote() error = %v", err)
+	}
+	current, err := reopened.Current()
+	if err != nil {
+		t.Fatalf("reopened Current() error = %v", err)
+	}
+
+	got := current.EntriesInPath([]string{"Root", "Internet"})
+	if len(got) != 1 {
+		t.Fatalf("len(EntriesInPath(Root/Internet)) = %d, want 1", len(got))
+	}
+	if got[0].Password != "local-token-2" || got[0].URL != "https://vault.crew.example.invalid/security/badges" {
+		t.Fatalf("entry after synchronize = %#v, want local winning version", got[0])
+	}
+	if len(got[0].History) == 0 {
+		t.Fatal("len(History) = 0, want overwritten remote variant preserved")
+	}
+	if got[0].History[0].Password != "remote-token-2" || got[0].History[0].Notes != "updated remotely first" {
+		t.Fatalf("History[0] = %#v, want displaced remote version first", got[0].History[0])
+	}
+}