diff --git a/base/files/file_win.cc b/base/files/file_win.cc
index 7a3f4cdefb05f0..085a7ee250d785 100644
--- a/base/files/file_win.cc
+++ b/base/files/file_win.cc
@@ -307,6 +307,9 @@ bool File::DeleteOnClose(bool delete_on_close) {
 File::Error File::OSErrorToFileError(DWORD last_error) {
   switch (last_error) {
     case ERROR_SHARING_VIOLATION:
+    case ERROR_UNABLE_TO_REMOVE_REPLACED:  // ReplaceFile failure cases.
+    case ERROR_UNABLE_TO_MOVE_REPLACEMENT:
+    case ERROR_UNABLE_TO_MOVE_REPLACEMENT_2:
       return FILE_ERROR_IN_USE;
     case ERROR_ALREADY_EXISTS:
     case ERROR_FILE_EXISTS:
@@ -315,6 +318,7 @@ File::Error File::OSErrorToFileError(DWORD last_error) {
     case ERROR_PATH_NOT_FOUND:
       return FILE_ERROR_NOT_FOUND;
     case ERROR_ACCESS_DENIED:
+    case ERROR_LOCK_VIOLATION:
       return FILE_ERROR_ACCESS_DENIED;
     case ERROR_TOO_MANY_OPEN_FILES:
       return FILE_ERROR_TOO_MANY_OPENED;
@@ -327,12 +331,14 @@ File::Error File::OSErrorToFileError(DWORD last_error) {
       return FILE_ERROR_NO_SPACE;
     case ERROR_USER_MAPPED_FILE:
       return FILE_ERROR_INVALID_OPERATION;
-    case ERROR_NOT_READY:
-    case ERROR_SECTOR_NOT_FOUND:
-    case ERROR_DEV_NOT_EXIST:
+    case ERROR_NOT_READY:         // The device is not ready.
+    case ERROR_SECTOR_NOT_FOUND:  // The drive cannot find the sector requested.
+    case ERROR_GEN_FAILURE:       // A device ... is not functioning.
+    case ERROR_DEV_NOT_EXIST:  // Net resource or device is no longer available.
     case ERROR_IO_DEVICE:
-    case ERROR_FILE_CORRUPT:
-    case ERROR_DISK_CORRUPT:
+    case ERROR_DISK_OPERATION_FAILED:
+    case ERROR_FILE_CORRUPT:  // File or directory is corrupted and unreadable.
+    case ERROR_DISK_CORRUPT:  // The disk structure is corrupted and unreadable.
       return FILE_ERROR_IO;
     default:
       UmaHistogramSparse("PlatformFile.UnknownErrors.Windows", last_error);
diff --git a/tools/metrics/histograms/enums.xml b/tools/metrics/histograms/enums.xml
index e3eb3aaf46f55e..1429d966434bce 100644
--- a/tools/metrics/histograms/enums.xml
+++ b/tools/metrics/histograms/enums.xml
@@ -90901,7 +90901,12 @@ Called by update_scheduler_enums.py.-->
   <int value="999" label="SWAPERROR"/>
   <int value="1011" label="ERROR_CANTOPEN"/>
   <int value="1117" label="ERROR_IO_DEVICE"/>
+  <int value="1127" label="DISK_OPERATION_FAILED"/>
+  <int value="1175" label="UNABLE_TO_REMOVE_REPLACED"/>
+  <int value="1176" label="UNABLE_TO_MOVE_REPLACEMENT"/>
+  <int value="1177" label="UNABLE_TO_MOVE_REPLACEMENT_2"/>
   <int value="1223" label="ERROR_CANCELLED"/>
+  <int value="1296" label="CONTENT_BLOCKED"/>
   <int value="1346" label="ERROR_BAD_IMPERSONATION_LEVEL"/>
   <int value="1392" label="ERROR_FILE_CORRUPT"/>
   <int value="1393" label="ERROR_DISK_CORRUPT"/>
@@ -90915,6 +90920,7 @@ Called by update_scheduler_enums.py.-->
   <int value="1784" label="INVALID_USER_BUFFER"/>
   <int value="1816" label="NOT_ENOUGH_QUOTA"/>
   <int value="1818" label="RPC_S_CALL_CANCELLED"/>
+  <int value="1920" label="CANT_ACCESS_FILE"/>
   <int value="6000" label="ERROR_ENCRYPTION_FAILED"/>
   <int value="6001" label="ERROR_DECRYPTION_FAILED"/>
   <int value="7041" label="ERROR_CTX_CONSOLE_DISCONNECT"/>