diff --git a/lib/oofatfs/ff.h b/lib/oofatfs/ff.h
index b133d770db..d77ddf5761 100644
--- a/lib/oofatfs/ff.h
+++ b/lib/oofatfs/ff.h
@@ -162,7 +162,7 @@ typedef struct {
     DWORD   bitbase;        /* Allocation bitmap base sector */
 #endif
     DWORD   winsect;        /* Current sector appearing in the win[] */
-    BYTE    win[FF_MAX_SS]; /* Disk access window for Directory, FAT (and file data at tiny cfg) */
+    __attribute__((aligned(FF_WINDOW_ALIGNMENT),)) BYTE    win[FF_MAX_SS]; /* Disk access window for Directory, FAT (and file data at tiny cfg). */
 } FATFS;
 
 
diff --git a/lib/oofatfs/ffconf.h b/lib/oofatfs/ffconf.h
index 52ff6d0a7a..2967244118 100644
--- a/lib/oofatfs/ffconf.h
+++ b/lib/oofatfs/ffconf.h
@@ -267,6 +267,12 @@
 /  for variable sector size mode and disk_ioctl() function needs to implement
 /  GET_SECTOR_SIZE command. */
 
+#ifdef MICROPY_FATFS_WINDOW_ALIGNMENT
+#define FF_WINDOW_ALIGNMENT   (MICROPY_FATFS_WINDOW_ALIGNMENT)
+#else
+#define FF_WINDOW_ALIGNMENT   1
+#endif
+
 
 #define FF_USE_TRIM     0
 /* This option switches support for ATA-TRIM. (0:Disable or 1:Enable)
diff --git a/lib/tinyusb b/lib/tinyusb
index 6c7c9f2ef5..db59494b1b 160000
--- a/lib/tinyusb
+++ b/lib/tinyusb
@@ -1 +1 @@
-Subproject commit 6c7c9f2ef5a80d5a6879e9c3558162188c6cf889
+Subproject commit db59494b1b24f7dad26c5c66c85a195a2cf09466
diff --git a/locale/circuitpython.pot b/locale/circuitpython.pot
index 9ebb85d13f..892b1368c4 100644
--- a/locale/circuitpython.pot
+++ b/locale/circuitpython.pot
@@ -1748,6 +1748,10 @@ msgstr ""
 msgid "Pins must share PWM slice"
 msgstr ""
 
+#: shared-module/usb/core/Device.c
+msgid "Pipe error"
+msgstr ""
+
 #: py/builtinhelp.c
 msgid "Plus any modules on the filesystem\n"
 msgstr ""
@@ -1825,7 +1829,8 @@ msgstr ""
 
 #: shared-bindings/_bleio/__init__.c
 #: shared-bindings/memorymonitor/AllocationSize.c
-#: shared-bindings/pulseio/PulseIn.c shared-module/displayio/Bitmap.c
+#: shared-bindings/pulseio/PulseIn.c shared-module/bitmaptools/__init__.c
+#: shared-module/displayio/Bitmap.c
 msgid "Read-only"
 msgstr ""
 
@@ -3985,7 +3990,7 @@ msgstr ""
 msgid "sosfilt requires iterable arguments"
 msgstr ""
 
-#: shared-bindings/bitmaptools/__init__.c shared-bindings/displayio/Bitmap.c
+#: shared-bindings/bitmaptools/__init__.c
 msgid "source palette too large"
 msgstr ""
 
diff --git a/ports/raspberrypi/lib/Pico-PIO-USB b/ports/raspberrypi/lib/Pico-PIO-USB
index 5a7aa8d4e7..d00a10a8c4 160000
--- a/ports/raspberrypi/lib/Pico-PIO-USB
+++ b/ports/raspberrypi/lib/Pico-PIO-USB
@@ -1 +1 @@
-Subproject commit 5a7aa8d4e78f9a50e4fb9defcf3488b3fc44aff1
+Subproject commit d00a10a8c425d0d40f81b87169102944b01f3bb3
diff --git a/py/circuitpy_mpconfig.h b/py/circuitpy_mpconfig.h
index e1909a064f..7e858212a5 100644
--- a/py/circuitpy_mpconfig.h
+++ b/py/circuitpy_mpconfig.h
@@ -611,6 +611,12 @@ void background_callback_run_all(void);
 #define CIRCUITPY_DIGITALIO_HAVE_INVALID_DRIVE_MODE (0)
 #endif
 
+// Align the internal sector buffer. Useful when it is passed into TinyUSB for
+// loads.
+#ifndef MICROPY_FATFS_WINDOW_ALIGNMENT
+#define MICROPY_FATFS_WINDOW_ALIGNMENT CIRCUITPY_TUSB_MEM_ALIGN
+#endif
+
 #define FF_FS_CASE_INSENSITIVE_COMPARISON_ASCII_ONLY (1)
 
 #define FF_FS_MAKE_VOLID (1)
diff --git a/shared-module/usb/core/Device.c b/shared-module/usb/core/Device.c
index 67756341ec..faed49e383 100644
--- a/shared-module/usb/core/Device.c
+++ b/shared-module/usb/core/Device.c
@@ -49,6 +49,7 @@ void tuh_umount_cb(uint8_t dev_addr) {
 }
 
 STATIC xfer_result_t _xfer_result;
+STATIC size_t _actual_len;
 bool common_hal_usb_core_device_construct(usb_core_device_obj_t *self, uint8_t device_number) {
     if (device_number == 0 || device_number > CFG_TUH_DEVICE_MAX + CFG_TUH_HUB) {
         return false;
@@ -78,6 +79,9 @@ uint16_t common_hal_usb_core_device_get_idProduct(usb_core_device_obj_t *self) {
 STATIC void _transfer_done_cb(tuh_xfer_t *xfer) {
     // Store the result so we stop waiting for the transfer.
     _xfer_result = xfer->result;
+    // The passed in xfer is not the original one we passed in, so we need to
+    // copy any info out that we want (like actual_len.)
+    _actual_len = xfer->actual_len;
 }
 
 STATIC bool _wait_for_callback(void) {
@@ -159,11 +163,14 @@ STATIC size_t _xfer(tuh_xfer_t *xfer, mp_int_t timeout) {
     }
     xfer_result_t result = _xfer_result;
     _xfer_result = 0xff;
-    if (result == XFER_RESULT_STALLED || result == 0xff) {
+    if (result == XFER_RESULT_STALLED) {
+        mp_raise_usb_core_USBError(translate("Pipe error"));
+    }
+    if (result == 0xff) {
         mp_raise_usb_core_USBTimeoutError();
     }
     if (result == XFER_RESULT_SUCCESS) {
-        return xfer->actual_len;
+        return _actual_len;
     }
 
     return 0;
@@ -192,7 +199,10 @@ STATIC bool _open_endpoint(usb_core_device_obj_t *self, mp_int_t endpoint) {
     }
     tusb_desc_configuration_t *desc_cfg = (tusb_desc_configuration_t *)desc_buf;
 
-    uint8_t const *desc_end = ((uint8_t const *)desc_cfg) + tu_le16toh(desc_cfg->wTotalLength);
+    uint32_t total_length = tu_le16toh(desc_cfg->wTotalLength);
+    // Cap to the buffer size we requested.
+    total_length = MIN(total_length, sizeof(desc_buf));
+    uint8_t const *desc_end = ((uint8_t const *)desc_cfg) + total_length;
     uint8_t const *p_desc = tu_desc_next(desc_cfg);
 
     // parse each interfaces
@@ -281,7 +291,10 @@ mp_int_t common_hal_usb_core_device_ctrl_transfer(usb_core_device_obj_t *self,
     }
     xfer_result_t result = _xfer_result;
     _xfer_result = 0xff;
-    if (result == XFER_RESULT_STALLED || result == 0xff) {
+    if (result == XFER_RESULT_STALLED) {
+        mp_raise_usb_core_USBError(translate("Pipe error"));
+    }
+    if (result == 0xff) {
         mp_raise_usb_core_USBTimeoutError();
     }
     if (result == XFER_RESULT_SUCCESS) {