diff --git a/gdb/symfile.c b/gdb/symfile.c
index 30147b7c3df..584a62cd1d6 100644
--- a/gdb/symfile.c
+++ b/gdb/symfile.c
@@ -2475,20 +2475,32 @@ reread_symbols (int from_tty)
       if (objfile->separate_debug_objfile_backlink)
 	continue;
 
-      /* If this object is from an archive (what you usually create with
-	 `ar', often called a `static library' on most systems, though
-	 a `shared library' on AIX is also an archive), then you should
-	 stat on the archive name, not member name.  */
-      const char *filename;
-      if (objfile->obfd->my_archive)
-	filename = bfd_get_filename (objfile->obfd->my_archive);
-      else
-	filename = objfile_name (objfile);
+      /* When a in-memory BFD is initially created, it's mtime (as
+	 returned by bfd_get_mtime) is the creation time of the BFD.
+	 However, we call bfd_stat here as we want to see if the
+	 underlying file has changed, and in this case an in-memory BFD
+	 will return an st_mtime of zero, so it appears that the in-memory
+	 file has changed, which isn't what we want here -- this code is
+	 about reloading BFDs that changed on disk.
+
+	 Just skip any in-memory BFD.  */
+      if (objfile->obfd.get ()->flags & BFD_IN_MEMORY)
+	continue;
 
       struct stat new_statbuf;
-      int res = stat (filename, &new_statbuf);
+      int res = bfd_stat (objfile->obfd.get (), &new_statbuf);
       if (res != 0)
 	{
+	  /* If this object is from an archive (what you usually create
+	     with `ar', often called a `static library' on most systems,
+	     though a `shared library' on AIX is also an archive), then you
+	     should stat on the archive name, not member name.  */
+	  const char *filename;
+	  if (objfile->obfd->my_archive)
+	    filename = bfd_get_filename (objfile->obfd->my_archive);
+	  else
+	    filename = objfile_name (objfile);
+
 	  warning (_("`%ps' has disappeared; keeping its symbols."),
 		   styled_string (file_name_style.style (), filename));
 	  continue;
diff --git a/gdb/testsuite/gdb.server/target-exec-file.c b/gdb/testsuite/gdb.server/target-exec-file.c
new file mode 100644
index 00000000000..3a264f239ed
--- /dev/null
+++ b/gdb/testsuite/gdb.server/target-exec-file.c
@@ -0,0 +1,22 @@
+/* This testcase is part of GDB, the GNU debugger.
+
+   Copyright 2023 Free Software Foundation, Inc.
+
+   This program is free software; you can redistribute it and/or modify
+   it under the terms of the GNU General Public License as published by
+   the Free Software Foundation; either version 3 of the License, or
+   (at your option) any later version.
+
+   This program is distributed in the hope that it will be useful,
+   but WITHOUT ANY WARRANTY; without even the implied warranty of
+   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+   GNU General Public License for more details.
+
+   You should have received a copy of the GNU General Public License
+   along with this program.  If not, see <http://www.gnu.org/licenses/>.  */
+
+int
+main ()
+{
+  return 0;
+}
diff --git a/gdb/testsuite/gdb.server/target-exec-file.exp b/gdb/testsuite/gdb.server/target-exec-file.exp
new file mode 100644
index 00000000000..9260df8b88d
--- /dev/null
+++ b/gdb/testsuite/gdb.server/target-exec-file.exp
@@ -0,0 +1,174 @@
+# This testcase is part of GDB, the GNU debugger.
+
+# Copyright 2023 Free Software Foundation, Inc.
+
+# This program is free software; you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation; either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program.  If not, see <http://www.gnu.org/licenses/>.
+
+# Test GDB's handling of using a file with a 'target:' prefix as the
+# executable file.  This test includes checking what happens when the
+# file on the target system changes and GDB needs to reload it.
+
+load_lib gdbserver-support.exp
+
+require allow_gdbserver_tests !use_gdb_stub
+
+standard_testfile
+
+if { [build_executable "failed to prepare" $testfile $srcfile debug] } {
+    return -1
+}
+
+clean_restart
+
+# Some boards specifically set the sysroot to the empty string to
+# avoid copying files from the target.  But for this test we do want
+# to copy files from the target, so set the sysroot back to 'target:'.
+#
+# This is fine so long as we're not using a board file that sets the
+# sysroot to something else -- but none of the standard boards do
+# this, and plenty of other tests mess with the sysroot, so I guess we
+# don't worry about that too much.
+gdb_test "set sysroot target:" ".*"
+
+# Make sure we're disconnected, in case we're testing with an
+# extended-remote board, therefore already connected.
+gdb_test "disconnect" ".*"
+
+# Ensure the executable is on the target.
+set target_exec [gdb_remote_download target $binfile]
+
+# We're going to be restarting the inferior.  Lets ask GDB not to
+# prompt us if this is the right thing to do.
+gdb_test_no_output "set confirm off"
+
+# Start gdbserver, but always in extended-remote mode, and then
+# connect to it from GDB.
+set res [gdbserver_start "--multi" $target_exec]
+set gdbserver_protocol "extended-remote"
+set gdbserver_gdbport [lindex $res 1]
+gdb_target_cmd $gdbserver_protocol $gdbserver_gdbport
+
+# Issue a 'file' command and parse the output.  We look for a couple
+# of specific things to ensure that we are correctly reading the exec
+# from the remote target.
+set saw_read_of_remote_exec false
+set saw_read_of_syms_from_exec false
+gdb_test_multiple "file target:$target_exec" "run file command" {
+    -re "^file target:\[^\r\n\]+\r\n" {
+	exp_continue
+    }
+
+    -re "^Reading (\[^\r\n\]+) from remote target\\.\\.\\.\r\n" {
+	set filename $expect_out(1,string)
+	if { $filename eq $target_exec } {
+	    set saw_read_of_remote_exec true
+	}
+	exp_continue
+    }
+
+    -re "^warning: File transfers from remote targets can be slow\[^\r\n\]+\r\n" {
+	exp_continue
+    }
+
+    -re "^Reading symbols from target:(\[^\r\n\]+)\\.\\.\\.\r\n" {
+	set filename $expect_out(1,string)
+	if { $filename eq $target_exec } {
+	    set saw_read_of_syms_from_exec true
+	}
+	exp_continue
+    }
+
+    -re "^Expanding full symbols from \[^\r\n\]+\r\n" {
+	exp_continue
+    }
+
+    -re "^$gdb_prompt $" {
+	pass $gdb_test_name
+    }
+}
+
+gdb_assert { $saw_read_of_remote_exec } \
+    "exec was read from the remote target"
+
+gdb_assert { $saw_read_of_syms_from_exec } \
+    "symbols were read from remote exec file"
+
+# Start the inferior (with the 'start' command), use TESTNAME for any
+# pass/fail calls.  EXPECT_REREAD should be true or false and
+# indicates if we expect to too a line like:
+#
+#  `FILE' has changed; re-reading symbols.
+proc start_inferior { testname expect_reread } {
+    with_test_prefix $testname {
+	if { [gdb_start_cmd] < 0 } {
+	    fail "start command"
+	    return -1
+	}
+
+	set saw_reread false
+	gdb_test_multiple "" "stopped at main" {
+	    -re "^start\\s*\r\n" {
+		exp_continue
+	    }
+	    -re "^`\[^\r\n\]+' has changed; re-reading symbols\\.\r\n" {
+		set saw_reread true
+		exp_continue
+	    }
+	    -re "^Reading \[^\r\n\]+ from remote target\\.\\.\\.\r\n" {
+		exp_continue
+	    }
+	    -re "^Expanding full symbols from \[^\r\n\]+\\.\\.\\.\r\n" {
+		exp_continue
+	    }
+	    -re "^Temporary breakpoint $::decimal at $::hex: \[^\r\n\]+\r\n" {
+		exp_continue
+	    }
+	    -re "^Starting program: \[^\r\n\]+\r\n" {
+		exp_continue
+	    }
+	    -re "^\\s*\r\n" {
+		exp_continue
+	    }
+	    -re "^Temporary breakpoint $::decimal, main \\(\\) at .*$::gdb_prompt $" {
+		pass $testname
+	    }
+	}
+
+	gdb_assert { $expect_reread == $saw_reread } \
+	    "check symbol re-read behaviour"
+    }
+}
+
+# Start the inferior for the first time.  The symbols were already
+# read from the file when the 'file' command was used, we should not
+# see the symbols re-read now.
+start_inferior "start inferior the first time" false
+
+# Re-start the inferior.  The executable is unchanged so we should not
+# see the symbol file being re-read.
+start_inferior "start inferior a second time" false
+
+# Delay for a short while so, when we touch the exec, we know the
+# timestamp will change.
+sleep 1
+set res [remote_exec target "touch $target_exec"]
+set status [lindex $res 0]
+if { $status != 0 } {
+    fail "touching executable on target"
+    return -1
+}
+
+# Start the inferior again, we expect to see the symbols being re-read
+# from the remote file.
+start_inferior "start inferior a third time" true