diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensions.kt b/app/src/main/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensions.kt
index 0bfa48501b..c18c4edda8 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensions.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensions.kt
@@ -163,13 +163,16 @@ private fun VaultAddEditState.ViewState.Content.toPasswordHistory(
     )
 
     return listOf(
-        common.originalCipher?.passwordHistory.orEmpty(),
         newPasswordHistory,
+        common.originalCipher?.passwordHistory.orEmpty(),
         newHiddenFieldHistory,
     )
         .flatten()
+        // Ensure that they are in the correct order before saving.
+        .sortedByDescending { it.lastUsedDate }
+        // Only persist the 5 most recent items.
+        .take(5)
         .ifEmpty { null }
-        ?.takeLast(5)
 }
 
 private fun getPasswordHistory(
diff --git a/app/src/test/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensionsTest.kt b/app/src/test/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensionsTest.kt
index 921f2bf40f..675f8e1677 100644
--- a/app/src/test/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensionsTest.kt
+++ b/app/src/test/kotlin/com/x8bit/bitwarden/ui/vault/feature/vault/util/VaultAddItemStateExtensionsTest.kt
@@ -18,8 +18,8 @@ import com.x8bit.bitwarden.data.vault.datasource.sdk.model.createMockSdkFido2Cre
 import com.x8bit.bitwarden.ui.vault.feature.addedit.VaultAddEditState
 import com.x8bit.bitwarden.ui.vault.feature.addedit.model.UriItem
 import com.x8bit.bitwarden.ui.vault.model.VaultCardBrand
-import com.x8bit.bitwarden.ui.vault.model.VaultCollection
 import com.x8bit.bitwarden.ui.vault.model.VaultCardExpirationMonth
+import com.x8bit.bitwarden.ui.vault.model.VaultCollection
 import com.x8bit.bitwarden.ui.vault.model.VaultIdentityTitle
 import com.x8bit.bitwarden.ui.vault.model.VaultLinkedFieldType
 import org.junit.jupiter.api.Assertions.assertEquals
@@ -202,11 +202,11 @@ class VaultAddItemStateExtensionsTest {
                 ),
                 passwordHistory = listOf(
                     PasswordHistoryView(
-                        password = "old_password",
+                        password = "password",
                         lastUsedDate = FIXED_CLOCK.instant(),
                     ),
                     PasswordHistoryView(
-                        password = "password",
+                        password = "old_password",
                         lastUsedDate = FIXED_CLOCK.instant(),
                     ),
                     PasswordHistoryView(
@@ -1104,11 +1104,11 @@ class VaultAddItemStateExtensionsTest {
                 fields = emptyList(),
                 passwordHistory = listOf(
                     PasswordHistoryView(
-                        password = "old_password",
+                        password = "password",
                         lastUsedDate = FIXED_CLOCK.instant(),
                     ),
                     PasswordHistoryView(
-                        password = "password",
+                        password = "old_password",
                         lastUsedDate = FIXED_CLOCK.instant(),
                     ),
                     PasswordHistoryView(