diff --git a/src/host/pico_stdio/include/pico/stdio.h b/src/host/pico_stdio/include/pico/stdio.h
index 5431853..de0bde1 100644
--- a/src/host/pico_stdio/include/pico/stdio.h
+++ b/src/host/pico_stdio/include/pico/stdio.h
@@ -16,6 +16,9 @@ void stdio_uart_init();
 static inline void stdio_init_all() { stdio_uart_init(); }
 static inline void stdio_filter_driver(stdio_driver_t *driver) {}
 static inline void stdio_set_translate_crlf(stdio_driver_t *driver, bool enabled) {}
+static inline bool stdio_usb_connected(void) { return true; }
 int getchar_timeout_us(uint32_t timeout_us);
+#define puts_raw puts
+#define putchar_raw putchar
 
 #endif
diff --git a/src/rp2_common/pico_stdio/include/pico/stdio.h b/src/rp2_common/pico_stdio/include/pico/stdio.h
index 9f01ae9..e44c01d 100644
--- a/src/rp2_common/pico_stdio/include/pico/stdio.h
+++ b/src/rp2_common/pico_stdio/include/pico/stdio.h
@@ -49,6 +49,9 @@ typedef struct stdio_driver stdio_driver_t;
  * Call this method once you have set up your clocks to enable the stdio support for UART, USB
  * and semihosting based on the presence of the respective libraries in the binary.
  *
+ * When stdio_usb is configured, this method can be optionally made to block, waiting for a connection
+ * via the variables specified in \ref stdio_usb_init (i.e. \ref PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS)
+ *
  * \see stdio_uart, stdio_usb, stdio_semihosting
  */
 void stdio_init_all(void);
@@ -74,7 +77,7 @@ int getchar_timeout_us(uint32_t timeout_us);
 /*! \brief Adds or removes a driver from the list of active drivers used for input/output
  * \ingroup pico_stdio
  *
- * \note this method should always be called on an initialized driver
+ * \note this method should always be called on an initialized driver and is not re-entrant
  * \param driver the driver
  * \param enabled true to add, false to remove
  */
@@ -100,6 +103,16 @@ void stdio_filter_driver(stdio_driver_t *driver);
  */
 void stdio_set_translate_crlf(stdio_driver_t *driver, bool translate);
 
+/*! \brief putchar variant that skips any CR/LF conversion if enabled
+ * \ingroup pico_stdio
+ */
+int putchar_raw(int c);
+
+/*! \brief puts variant that skips any CR/LF conversion if enabled
+ * \ingroup pico_stdio
+ */
+int puts_raw(const char *s);
+
 #ifdef __cplusplus
 }
 #endif
diff --git a/src/rp2_common/pico_stdio/stdio.c b/src/rp2_common/pico_stdio/stdio.c
index bf10ad6..8dd7257 100644
--- a/src/rp2_common/pico_stdio/stdio.c
+++ b/src/rp2_common/pico_stdio/stdio.c
@@ -59,6 +59,9 @@ static bool stdout_serialize_begin(void) {
 static void stdout_serialize_end(void) {
 }
 #endif
+static void stdio_out_chars_no_crlf(stdio_driver_t *driver, const char *s, int len) {
+    driver->out_chars(s, len);
+}
 
 static void stdio_out_chars_crlf(stdio_driver_t *driver, const char *s, int len) {
 #if PICO_STDIO_ENABLE_CRLF_SUPPORT
@@ -89,7 +92,7 @@ static void stdio_out_chars_crlf(stdio_driver_t *driver, const char *s, int len)
 #endif
 }
 
-static bool stdio_put_string(const char *s, int len, bool newline) {
+static bool stdio_put_string(const char *s, int len, bool newline, bool no_cr) {
     bool serialized = stdout_serialize_begin();
     if (!serialized) {
 #if PICO_STDIO_IGNORE_NESTED_STDOUT
@@ -97,13 +100,14 @@ static bool stdio_put_string(const char *s, int len, bool newline) {
 #endif
     }
     if (len == -1) len = (int)strlen(s);
+    void (*out_func)(stdio_driver_t *, const char *, int) = no_cr ? stdio_out_chars_no_crlf : stdio_out_chars_crlf;
     for (stdio_driver_t *driver = drivers; driver; driver = driver->next) {
         if (!driver->out_chars) continue;
         if (filter && filter != driver) continue;
-        stdio_out_chars_crlf(driver, s, len);
+        out_func(driver, s, len);
         if (newline) {
             const char c = '\n';
-            stdio_out_chars_crlf(driver, &c, 1);
+            out_func(driver, &c, 1);
         }
     }
     if (serialized) {
@@ -134,13 +138,26 @@ static int stdio_get_until(char *buf, int len, absolute_time_t until) {
 
 int WRAPPER_FUNC(putchar)(int c) {
     char cc = (char)c;
-    stdio_put_string(&cc, 1, false);
+    stdio_put_string(&cc, 1, false, false);
     return c;
 }
 
 int WRAPPER_FUNC(puts)(const char *s) {
     int len = (int)strlen(s);
-    stdio_put_string(s, len, true);
+    stdio_put_string(s, len, true, false);
+    stdio_flush();
+    return len;
+}
+
+int putchar_raw(int c) {
+    char cc = (char)c;
+    stdio_put_string(&cc, 1, false, true);
+    return c;
+}
+
+int puts_raw(const char *s) {
+    int len = (int)strlen(s);
+    stdio_put_string(s, len, true, true);
     stdio_flush();
     return len;
 }
@@ -154,7 +171,7 @@ int _read(int handle, char *buffer, int length) {
 
 int _write(int handle, char *buffer, int length) {
     if (handle == 1) {
-        stdio_put_string(buffer, length, false);
+        stdio_put_string(buffer, length, false, false);
         return length;
     }
     return -1;
@@ -243,7 +260,7 @@ int __printflike(1, 0) WRAPPER_FUNC(printf)(const char* format, ...)
     return ret;
 }
 
-void stdio_init_all() {
+void stdio_init_all(void) {
     // todo add explicit custom, or registered although you can call stdio_enable_driver explicitly anyway
     // These are well known ones
 #if LIB_PICO_STDIO_UART
diff --git a/src/rp2_common/pico_stdio_usb/include/pico/stdio_usb.h b/src/rp2_common/pico_stdio_usb/include/pico/stdio_usb.h
index 6a1effa..db63142 100644
--- a/src/rp2_common/pico_stdio_usb/include/pico/stdio_usb.h
+++ b/src/rp2_common/pico_stdio_usb/include/pico/stdio_usb.h
@@ -54,6 +54,16 @@
 #define PICO_STDIO_USB_RESET_MAGIC_BAUD_RATE 1200
 #endif
 
+// PICO_CONFIG: PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS, Maximum number of milliseconds to wait during initialization for a CDC connection from the host (negative means indefinite) before returning, default=0, group=pico_stdio_usb
+#ifndef PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS
+#define PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS 0
+#endif
+
+// PICO_CONFIG: PICO_STDIO_USB_POST_CONNECT_WAIT_DELAY_MS, Number of milliseconds to wait during initialization after a host CDC connection is detected before returning (some host terminals seem to sometimes lose transmissions sent right after connection), default=50, group=pico_stdio_usb
+#ifndef PICO_STDIO_USB_POST_CONNECT_WAIT_DELAY_MS
+#define PICO_STDIO_USB_POST_CONNECT_WAIT_DELAY_MS 50
+#endif
+
 // PICO_CONFIG: PICO_STDIO_USB_RESET_BOOTSEL_ACTIVITY_LED, Optionally define a pin to use as bootloader activity LED when BOOTSEL mode is entered via USB (either VIA_BAUD_RATE or VIA_VENDOR_INTERFACE), type=int, min=0, max=29, group=pico_stdio_usb
 
 // PICO_CONFIG: PICO_STDIO_USB_RESET_BOOTSEL_FIXED_ACTIVITY_LED, Whether the pin specified by PICO_STDIO_USB_RESET_BOOTSEL_ACTIVITY_LED is fixed or can be modified by picotool over the VENDOR USB interface, type=bool, default=0, group=pico_stdio_usb
@@ -94,10 +104,22 @@ extern "C" {
 extern stdio_driver_t stdio_usb;
 
 /*! \brief Explicitly initialize USB stdio and add it to the current set of stdin drivers
- *  \ingroup pico_stdio_uart
+ *  \ingroup pico_stdio_usb
+ *
+ *  \ref PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS can be set to cause this method to wait for a CDC connection
+ *  from the host before returning, which is useful if you don't want any initial stdout output to be discarded
+ *  before the connection is established.
+ *
+ *  \return true if the USB CDC was initialized, false if an error occurred
  */
 bool stdio_usb_init(void);
 
+/*! \brief Check if there is an active stdio CDC connection to a host
+ *  \ingroup pico_stdio_usb
+ *
+ *  \return true if stdio is connected over CDC
+ */
+bool stdio_usb_connected(void);
 #ifdef __cplusplus
 }
 #endif
diff --git a/src/rp2_common/pico_stdio_usb/stdio_usb.c b/src/rp2_common/pico_stdio_usb/stdio_usb.c
index 2cca2c2..42ea4df 100644
--- a/src/rp2_common/pico_stdio_usb/stdio_usb.c
+++ b/src/rp2_common/pico_stdio_usb/stdio_usb.c
@@ -103,9 +103,29 @@ bool stdio_usb_init(void) {
     bool rc = add_alarm_in_us(PICO_STDIO_USB_TASK_INTERVAL_US, timer_task, NULL, true);
     if (rc) {
         stdio_set_driver_enabled(&stdio_usb, true);
+#if PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS
+#if PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS > 0
+        absolute_time_t until = make_timeout_time_ms(PICO_STDIO_USB_CONNECT_WAIT_TIMEOUT_MS);
+#else
+        absolute_time_t until = at_the_end_of_time;
+#endif
+        do {
+            if (stdio_usb_connected()) {
+#if PICO_STDIO_USB_POST_CONNECT_WAIT_DELAY_MS != 0
+                sleep_ms(PICO_STDIO_USB_POST_CONNECT_WAIT_DELAY_MS);
+#endif
+                break;
+            }
+            sleep_ms(10);
+        } while (!time_reached(until));
+#endif
     }
     return rc;
 }
+
+bool stdio_usb_connected(void) {
+    return tud_cdc_connected();
+}
 #else
 #include "pico/stdio_usb.h"
 #warning stdio USB was configured, but is being disabled as TinyUSB is explicitly linked