diff --git a/changes/ticket32622 b/changes/ticket32622
new file mode 100644
index 0000000000..1c663567fd
--- /dev/null
+++ b/changes/ticket32622
@@ -0,0 +1,5 @@
+  o Minor features (bootstrap reporting):
+    - Report more detailed reasons for bootstrap failure when the failure
+      happens due to a TLS error. Previously we would just call these errors
+      "MISC" when they happened during read, and "DONE" when they
+      happened during any other TLS operation. Closes ticket 32622.
diff --git a/src/core/mainloop/connection.c b/src/core/mainloop/connection.c
index a8417e46d9..792cdbf686 100644
--- a/src/core/mainloop/connection.c
+++ b/src/core/mainloop/connection.c
@@ -4205,6 +4205,7 @@ connection_handle_write_impl(connection_t *conn, int force)
     switch (result) {
       CASE_TOR_TLS_ERROR_ANY:
       case TOR_TLS_CLOSE:
+        or_conn->tls_error = result;
         log_info(LD_NET, result != TOR_TLS_CLOSE ?
                  "tls error. breaking.":"TLS connection closed on flush");
         /* Don't flush; connection is dead. */
diff --git a/src/core/or/connection_or.c b/src/core/or/connection_or.c
index 5d71b363f8..b88d1b6afb 100644
--- a/src/core/or/connection_or.c
+++ b/src/core/or/connection_or.c
@@ -745,10 +745,16 @@ connection_or_about_to_close(or_connection_t *or_conn)
         int reason = tls_error_to_orconn_end_reason(or_conn->tls_error);
         connection_or_event_status(or_conn, OR_CONN_EVENT_FAILED,
                                    reason);
-        if (!authdir_mode_tests_reachability(options))
-          control_event_bootstrap_prob_or(
-                orconn_end_reason_to_control_string(reason),
-                reason, or_conn);
+        if (!authdir_mode_tests_reachability(options)) {
+          const char *warning = NULL;
+          if (reason == END_OR_CONN_REASON_TLS_ERROR && or_conn->tls) {
+            warning = tor_tls_get_last_error_msg(or_conn->tls);
+          }
+          if (warning == NULL) {
+            warning = orconn_end_reason_to_control_string(reason);
+          }
+          control_event_bootstrap_prob_or(warning, reason, or_conn);
+        }
       }
     }
   } else if (conn->hold_open_until_flushed) {
@@ -1692,7 +1698,8 @@ connection_tls_continue_handshake(or_connection_t *conn)
 
   switch (result) {
     CASE_TOR_TLS_ERROR_ANY:
-    log_info(LD_OR,"tls error [%s]. breaking connection.",
+      conn->tls_error = result;
+      log_info(LD_OR,"tls error [%s]. breaking connection.",
              tor_tls_err_to_string(result));
       return -1;
     case TOR_TLS_DONE:
@@ -1724,6 +1731,7 @@ connection_tls_continue_handshake(or_connection_t *conn)
       log_debug(LD_OR,"wanted read");
       return 0;
     case TOR_TLS_CLOSE:
+      conn->tls_error = result;
       log_info(LD_OR,"tls closed. breaking connection.");
       return -1;
   }
diff --git a/src/core/or/or.h b/src/core/or/or.h
index 5b35cbe7f1..8758a2ec6f 100644
--- a/src/core/or/or.h
+++ b/src/core/or/or.h
@@ -220,7 +220,8 @@ struct curve25519_public_key_t;
 #define END_OR_CONN_REASON_IO_ERROR       7 /* read/write error */
 #define END_OR_CONN_REASON_RESOURCE_LIMIT 8 /* sockets, buffers, etc */
 #define END_OR_CONN_REASON_PT_MISSING     9 /* PT failed or not available */
-#define END_OR_CONN_REASON_MISC           10
+#define END_OR_CONN_REASON_TLS_ERROR      10 /* Problem in TLS protocol */
+#define END_OR_CONN_REASON_MISC           11
 
 /* Reasons why we (or a remote OR) might close a stream. See tor-spec.txt for
  * documentation of these.  The values must match. */
diff --git a/src/core/or/reasons.c b/src/core/or/reasons.c
index 7da7843cab..708f43a689 100644
--- a/src/core/or/reasons.c
+++ b/src/core/or/reasons.c
@@ -244,6 +244,8 @@ orconn_end_reason_to_control_string(int r)
       return "IOERROR";
     case END_OR_CONN_REASON_RESOURCE_LIMIT:
       return "RESOURCELIMIT";
+    case END_OR_CONN_REASON_TLS_ERROR:
+      return "TLS_ERROR";
     case END_OR_CONN_REASON_MISC:
       return "MISC";
     case END_OR_CONN_REASON_PT_MISSING:
@@ -276,6 +278,8 @@ tls_error_to_orconn_end_reason(int e)
     case TOR_TLS_CLOSE:
     case TOR_TLS_DONE:
       return END_OR_CONN_REASON_DONE;
+    case TOR_TLS_ERROR_MISC:
+      return END_OR_CONN_REASON_TLS_ERROR;
     default:
       return END_OR_CONN_REASON_MISC;
   }
diff --git a/src/lib/tls/tortls.h b/src/lib/tls/tortls.h
index e8dbbf5279..517cdc17dd 100644
--- a/src/lib/tls/tortls.h
+++ b/src/lib/tls/tortls.h
@@ -81,6 +81,7 @@ void tor_tls_free_all(void);
 void tor_tls_init(void);
 void tls_log_errors(tor_tls_t *tls, int severity, int domain,
                     const char *doing);
+const char *tor_tls_get_last_error_msg(const tor_tls_t *tls);
 int tor_tls_context_init(unsigned flags,
                          crypto_pk_t *client_identity,
                          crypto_pk_t *server_identity,
diff --git a/src/lib/tls/tortls_nss.c b/src/lib/tls/tortls_nss.c
index 62e8262115..a9ec731c0a 100644
--- a/src/lib/tls/tortls_nss.c
+++ b/src/lib/tls/tortls_nss.c
@@ -369,6 +369,8 @@ tls_log_errors(tor_tls_t *tls, int severity, int domain,
 
   (void)tls;
   PRErrorCode code = PORT_GetError();
+  if (tls)
+    tls->last_error = code;
 
   const char *addr = tls ? tls->address : NULL;
   const char *string = PORT_ErrorToString(code);
@@ -391,6 +393,17 @@ tls_log_errors(tor_tls_t *tls, int severity, int domain,
            with, addr);
   }
 }
+const char *
+tor_tls_get_last_error_msg(const tor_tls_t *tls)
+{
+  IF_BUG_ONCE(!tls) {
+    return NULL;
+  }
+  if (tls->last_error == 0) {
+    return NULL;
+  }
+  return PORT_ErrorToString((PRErrorCode)tls->last_error);
+}
 
 tor_tls_t *
 tor_tls_new(tor_socket_t sock, int is_server)
diff --git a/src/lib/tls/tortls_openssl.c b/src/lib/tls/tortls_openssl.c
index 68d6e2aa50..2269714141 100644
--- a/src/lib/tls/tortls_openssl.c
+++ b/src/lib/tls/tortls_openssl.c
@@ -245,10 +245,30 @@ tls_log_errors(tor_tls_t *tls, int severity, int domain, const char *doing)
   unsigned long err;
 
   while ((err = ERR_get_error()) != 0) {
+    if (tls)
+      tls->last_error = err;
     tor_tls_log_one_error(tls, err, severity, domain, doing);
   }
 }
 
+/**
+ * Return a string representing more detail about the last error received
+ * on TLS.
+ *
+ * May return null if no error was found.
+ **/
+const char *
+tor_tls_get_last_error_msg(const tor_tls_t *tls)
+{
+  IF_BUG_ONCE(!tls) {
+    return NULL;
+  }
+  if (tls->last_error == 0) {
+    return NULL;
+  }
+  return (const char*)ERR_reason_error_string(tls->last_error);
+}
+
 #define CATCH_SYSCALL 1
 #define CATCH_ZERO    2
 
diff --git a/src/lib/tls/tortls_st.h b/src/lib/tls/tortls_st.h
index 925896d493..34abe52ee3 100644
--- a/src/lib/tls/tortls_st.h
+++ b/src/lib/tls/tortls_st.h
@@ -67,6 +67,8 @@ struct tor_tls_t {
    */
   unsigned long last_write_count;
   unsigned long last_read_count;
+  /** Most recent error value from ERR_get_error(). */
+  unsigned long last_error;
   /** If set, a callback to invoke whenever the client tries to renegotiate
    * the handshake. */
   void (*negotiated_callback)(tor_tls_t *tls, void *arg);
@@ -77,6 +79,7 @@ struct tor_tls_t {
   /** Last values retried from tor_get_prfiledesc_byte_counts(). */
   uint64_t last_write_count;
   uint64_t last_read_count;
+  long last_error;
 #endif
 };