diff --git a/gdb/completer.c b/gdb/completer.c
index 1008ec2..93eb8db 100644
--- a/gdb/completer.c
+++ b/gdb/completer.c
@@ -182,6 +182,17 @@ static const char gdb_completer_file_name_break_characters[] =
   " \t\n*|\"';:?><";
 #endif
 
+/* When completing on file names, for commands that don't accept quoted
+   file names, the only character that can be used as a word separator is
+   the path separator.  Every other character is treated as a literal
+   character within the filename.  */
+static const char gdb_completer_path_break_characters[] =
+#ifdef HAVE_DOS_BASED_FILE_SYSTEM
+  ";";
+#else
+  ":";
+#endif
+
 /* Characters that can be used to quote expressions.  Note that we can't
    include '"' (double quote) because the gdb C parser treats such quoted
    sequences as strings.  */
@@ -203,15 +214,15 @@ noop_completer (struct cmd_list_element *ignore,
 {
 }
 
-/* Complete on filenames.  */
+/* Generate filename completions of WORD, storing the completions into
+   TRACKER.  This is used for generating completions for commands that
+   only accept unquoted filenames as well as for commands that accept
+   quoted and escaped filenames.  */
 
-void
-filename_completer (struct cmd_list_element *ignore,
-		    completion_tracker &tracker,
-		    const char *text, const char *word)
+static void
+filename_completer_generate_completions (completion_tracker &tracker,
+					 const char *word)
 {
-  rl_completer_quote_characters = gdb_completer_file_name_quote_characters;
-
   int subsequent_name = 0;
   while (1)
     {
@@ -249,13 +260,13 @@ filename_completer (struct cmd_list_element *ignore,
     }
 }
 
-/* The corresponding completer_handle_brkchars
-   implementation.  */
+/* The brkchars callback used when completing filenames that can be
+   quoted.  */
 
 static void
-filename_completer_handle_brkchars (struct cmd_list_element *ignore,
-				    completion_tracker &tracker,
-				    const char *text, const char *word)
+filename_maybe_quoted_completer_handle_brkchars
+	(struct cmd_list_element *ignore, completion_tracker &tracker,
+	 const char *text, const char *word)
 {
   set_rl_completer_word_break_characters
     (gdb_completer_file_name_break_characters);
@@ -263,6 +274,50 @@ filename_completer_handle_brkchars (struct cmd_list_element *ignore,
   rl_completer_quote_characters = gdb_completer_file_name_quote_characters;
 }
 
+/* Complete on filenames.  This is for commands that accepts possibly
+   quoted filenames.  */
+
+void
+filename_maybe_quoted_completer (struct cmd_list_element *ignore,
+				 completion_tracker &tracker,
+				 const char *text, const char *word)
+{
+  filename_maybe_quoted_completer_handle_brkchars (ignore, tracker,
+						   text, word);
+  filename_completer_generate_completions (tracker, word);
+}
+
+/* The brkchars callback used by commands that don't accept quoted
+   filenames.  */
+
+static void
+filename_completer_handle_brkchars
+	(struct cmd_list_element *ignore, completion_tracker &tracker,
+	 const char *text, const char *word)
+{
+  gdb_assert (word == nullptr);
+
+  set_rl_completer_word_break_characters (gdb_completer_path_break_characters);
+  rl_completer_quote_characters = nullptr;
+  rl_filename_quoting_desired = 0;
+
+  tracker.set_use_custom_word_point (true);
+  word = advance_to_filename_complete_word_point (tracker, text);
+  filename_completer (ignore, tracker, text, word);
+}
+
+/* See completer.h.  */
+
+void
+filename_completer
+	(struct cmd_list_element *ignore, completion_tracker &tracker,
+	 const char *text, const char *word)
+{
+  gdb_assert (tracker.use_custom_word_point ());
+  gdb_assert (word != nullptr);
+  filename_completer_generate_completions (tracker, word);
+}
+
 /* Find the bounds of the current word for completion purposes, and
    return a pointer to the end of the word.  This mimics (and is a
    modified version of) readline's _rl_find_completion_word internal
@@ -447,8 +502,8 @@ const char *
 advance_to_filename_complete_word_point (completion_tracker &tracker,
 					 const char *text)
 {
-  const char *brk_chars = gdb_completer_file_name_break_characters;
-  const char *quote_chars = gdb_completer_file_name_quote_characters;
+  const char *brk_chars = gdb_completer_path_break_characters;
+  const char *quote_chars = nullptr;
   return advance_to_completion_word (tracker, brk_chars, quote_chars, text);
 }
 
@@ -1880,6 +1935,9 @@ completer_handle_brkchars_func_for_completer (completer_ftype *fn)
   if (fn == filename_completer)
     return filename_completer_handle_brkchars;
 
+  if (fn == filename_maybe_quoted_completer)
+    return filename_maybe_quoted_completer_handle_brkchars;
+
   if (fn == location_completer)
     return location_completer_handle_brkchars;
 
diff --git a/gdb/completer.h b/gdb/completer.h
index 98a12f3..c6d064e 100644
--- a/gdb/completer.h
+++ b/gdb/completer.h
@@ -563,9 +563,10 @@ extern completion_result
 const char *advance_to_expression_complete_word_point
   (completion_tracker &tracker, const char *text);
 
-/* Assuming TEXT is an filename, find the completion word point for
-   TEXT, emulating the algorithm readline uses to find the word
-   point.  */
+/* Assuming TEXT is a filename, find the completion word point for TEXT,
+   emulating the algorithm readline uses to find the word point.  The
+   filenames that are located by this function assume no filename
+   quoting, this function should be paired with filename_completer.  */
 extern const char *advance_to_filename_complete_word_point
   (completion_tracker &tracker, const char *text);
 
@@ -573,10 +574,27 @@ extern void noop_completer (struct cmd_list_element *,
 			    completion_tracker &tracker,
 			    const char *, const char *);
 
+/* Filename completer for commands that don't accept quoted filenames.
+   This completer does support completing a list of filenames that are
+   separated with the path separator (':' for UNIX and ';' for MS-DOS).
+
+   When adding a new command it is better to write the command so it
+   accepts quoted filenames and use filename_maybe_quoted_completer, for
+   examples see the 'exec' and 'exec-file' commands.  */
+
 extern void filename_completer (struct cmd_list_element *,
 				completion_tracker &tracker,
 				const char *, const char *);
 
+/* Filename completer for commands where the filename argument can be
+   quoted.  This completer also supports completing a list of filenames
+   that are separated with the path separator (':' for UNIX and ';' for
+   MS-DOS).  */
+
+extern void filename_maybe_quoted_completer (struct cmd_list_element *,
+					     completion_tracker &tracker,
+					     const char *, const char *);
+
 extern void expression_completer (struct cmd_list_element *,
 				  completion_tracker &tracker,
 				  const char *, const char *);
diff --git a/gdb/exec.c b/gdb/exec.c
index 683b0a1..38ce461 100644
--- a/gdb/exec.c
+++ b/gdb/exec.c
@@ -1074,14 +1074,14 @@ and it is the program executed when you use the `run' command.\n\
 If FILE cannot be found as specified, your execution directory path\n\
 ($PATH) is searched for a command of that name.\n\
 No arg means to have no executable file and no symbols."), &cmdlist);
-  set_cmd_completer (c, filename_completer);
+  set_cmd_completer (c, filename_maybe_quoted_completer);
 
   c = add_cmd ("exec-file", class_files, exec_file_command, _("\
 Use FILE as program for getting contents of pure memory.\n\
 If FILE cannot be found as specified, your execution directory path\n\
 is searched for a command of that name.\n\
 No arg means have no executable file."), &cmdlist);
-  set_cmd_completer (c, filename_completer);
+  set_cmd_completer (c, filename_maybe_quoted_completer);
 
   add_com ("section", class_files, set_section_command, _("\
 Change the base address of section SECTION of the exec file to ADDR.\n\
diff --git a/gdb/guile/scm-cmd.c b/gdb/guile/scm-cmd.c
index 2a55076..8255529 100644
--- a/gdb/guile/scm-cmd.c
+++ b/gdb/guile/scm-cmd.c
@@ -110,7 +110,7 @@ struct cmdscm_completer
 static const struct cmdscm_completer cmdscm_completers[] =
 {
   { "COMPLETE_NONE", noop_completer },
-  { "COMPLETE_FILENAME", filename_completer },
+  { "COMPLETE_FILENAME", filename_maybe_quoted_completer },
   { "COMPLETE_LOCATION", location_completer },
   { "COMPLETE_COMMAND", command_completer },
   { "COMPLETE_SYMBOL", symbol_completer },
diff --git a/gdb/python/py-cmd.c b/gdb/python/py-cmd.c
index 2ce2c90..e042f20 100644
--- a/gdb/python/py-cmd.c
+++ b/gdb/python/py-cmd.c
@@ -39,7 +39,7 @@ struct cmdpy_completer
 static const struct cmdpy_completer completers[] =
 {
   { "COMPLETE_NONE", noop_completer },
-  { "COMPLETE_FILENAME", filename_completer },
+  { "COMPLETE_FILENAME", filename_maybe_quoted_completer },
   { "COMPLETE_LOCATION", location_completer },
   { "COMPLETE_COMMAND", command_completer },
   { "COMPLETE_SYMBOL", symbol_completer },
diff --git a/gdb/symfile.c b/gdb/symfile.c
index cf7ab0b..c3cd961 100644
--- a/gdb/symfile.c
+++ b/gdb/symfile.c
@@ -3814,7 +3814,7 @@ Usage: symbol-file [-readnow | -readnever] [-o OFF] FILE\n\
 OFF is an optional offset which is added to each section address.\n\
 The `file' command can also load symbol tables, as well as setting the file\n\
 to execute.\n" READNOW_READNEVER_HELP), &cmdlist);
-  set_cmd_completer (c, filename_completer);
+  set_cmd_completer (c, filename_maybe_quoted_completer);
 
   c = add_cmd ("add-symbol-file", class_files, add_symbol_file_command, _("\
 Load symbols from FILE, assuming FILE has been dynamically loaded.\n\
@@ -3828,7 +3828,7 @@ OFF is an optional offset which is added to the default load addresses\n\
 of all sections for which no other address was specified.\n"
 READNOW_READNEVER_HELP),
 	       &cmdlist);
-  set_cmd_completer (c, filename_completer);
+  set_cmd_completer (c, filename_maybe_quoted_completer);
 
   c = add_cmd ("remove-symbol-file", class_files,
 	       remove_symbol_file_command, _("\
diff --git a/gdb/testsuite/gdb.base/filename-completion.exp b/gdb/testsuite/gdb.base/filename-completion.exp
index b700977..37629bf 100644
--- a/gdb/testsuite/gdb.base/filename-completion.exp
+++ b/gdb/testsuite/gdb.base/filename-completion.exp
@@ -23,8 +23,16 @@
 #
 # root/			[ DIRECTORY ]
 #   aaa/		[ DIRECTORY ]
+#     aa bb		[ FILE ]
+#     aa cc		[ FILE ]
+#   aaa/		[ DIRECTORY ]
 #   bb1/		[ DIRECTORY ]
 #   bb2/		[ DIRECTORY ]
+#     dir 1/		[ DIRECTORY ]
+#       unique file	[ FILE ]
+#     dir 2/		[ DIRECTORY ]
+#       file 1		[ FILE ]
+#       file 2		[ FILE ]
 #   cc1/		[ DIRECTORY ]
 #   cc2			[ FILE ]
 proc setup_directory_tree {} {
@@ -36,68 +44,170 @@
     remote_exec host "mkdir -p ${root}/bb2"
     remote_exec host "mkdir -p ${root}/cc1"
     remote_exec host "touch ${root}/cc2"
-
     remote_exec host "touch \"${root}/aaa/aa bb\""
     remote_exec host "touch \"${root}/aaa/aa cc\""
+    remote_exec host "mkdir -p \"${root}/bb2/dir 1\""
+    remote_exec host "mkdir -p \"${root}/bb2/dir 2\""
+    remote_exec host "touch \"${root}/bb2/dir 1/unique file\""
+    remote_exec host "touch \"${root}/bb2/dir 2/file 1\""
+    remote_exec host "touch \"${root}/bb2/dir 2/file 2\""
 
     return $root
 }
 
-# Run filename completetion tests.  ROOT is the base directory as
-# returned from setup_directory_tree, though, if ROOT is a
-# sub-directory of the user's home directory ROOT might have been
-# modified to replace the $HOME prefix with a single "~" character.
-proc run_tests { root } {
+# Run filename completetion tests for those command that accept quoting and
+# escaping of the filename argument.
+#
+# ROOT is the base directory as returned from setup_directory_tree, though,
+# if ROOT is a sub-directory of the user's home directory ROOT might have
+# been modified to replace the $HOME prefix with a single "~" character.
+proc run_quoting_and_escaping_tests { root } {
+    # Test all the commands which allow quoting of filenames, and
+    # which require whitespace to be escaped in unquoted filenames.
+    foreach_with_prefix cmd { file exec-file symbol-file add-symbol-file } {
+	gdb_start
 
-    # Completing 'thread apply all ...' commands uses a custom word
-    # point.  At one point we had a bug where doing this would break
-    # completion of quoted filenames that contained white space.
-    test_gdb_complete_unique "thread apply all hel" \
-	"thread apply all help" " " false \
-	"complete a 'thread apply all' command"
+	# Completing 'thread apply all ...' commands uses a custom word
+	# point.  At one point we had a bug where doing this would break
+	# completion of quoted filenames that contained white space.
+	test_gdb_complete_unique "thread apply all hel" \
+	    "thread apply all help" " " false \
+	    "complete a 'thread apply all' command"
 
-    foreach_with_prefix qc [list "" "'" "\""] {
-	test_gdb_complete_none "file ${qc}${root}/xx" \
-	    "expand a non-existent filename"
+	foreach_with_prefix qc [list "" "'" "\""] {
+	    test_gdb_complete_none "$cmd ${qc}${root}/xx" \
+		"expand a non-existent filename"
 
-	test_gdb_complete_unique "file ${qc}${root}/a" \
-	    "file ${qc}${root}/aaa/" "" false \
-	    "expand a unique filename"
+	    test_gdb_complete_unique "$cmd ${qc}${root}/a" \
+		"$cmd ${qc}${root}/aaa/" "" false \
+		"expand a unique filename"
 
-	test_gdb_complete_multiple "file ${qc}${root}/" \
-	    "b" "b" {
-		"bb1/"
-		"bb2/"
-	    } "" "${qc}" false \
-	    "expand multiple directory names"
-
-	test_gdb_complete_multiple "file ${qc}${root}/" \
-	    "c" "c" {
-		"cc1/"
-		"cc2"
-	    } "" "${qc}" false \
-	    "expand mixed directory and file names"
-
-	# GDB does not currently escape word break characters
-	# (e.g. white space) correctly in unquoted filenames.
-	if { $qc ne "" } {
-	    set sp " "
-
-	    test_gdb_complete_multiple "file ${qc}${root}/aaa/" \
-		"a" "a${sp}" {
-		    "aa bb"
-		    "aa cc"
+	    test_gdb_complete_multiple "$cmd ${qc}${root}/" \
+		"b" "b" {
+		    "bb1/"
+		    "bb2/"
 		} "" "${qc}" false \
-		"expand filenames containing spaces"
+		"expand multiple directory names"
+
+	    test_gdb_complete_multiple "$cmd ${qc}${root}/" \
+		"c" "c" {
+		    "cc1/"
+		    "cc2"
+		} "" "${qc}" false \
+		"expand mixed directory and file names"
+
+	    # GDB does not currently escape word break characters
+	    # (e.g. white space) correctly in unquoted filenames.
+	    if { $qc ne "" } {
+		set sp " "
+
+		test_gdb_complete_multiple "$cmd ${qc}${root}/aaa/" \
+		    "a" "a${sp}" {
+			"aa bb"
+			"aa cc"
+		    } "" "${qc}" false \
+		    "expand filenames containing spaces"
+	    }
+	}
+
+	gdb_exit
+    }
+}
+
+# Helper for run_unquoted_tests.  ROOT is the root directory as setup
+# by setup_directory_tree.  CMD is the GDB command to test.  PREFIX is
+# a possible prefix filename to prepend to the filename being
+# completed.
+proc run_unquoted_tests_core { root cmd { prefix "" } } {
+    gdb_start
+
+    if { $prefix != "" } {
+	# Platform specific path separator (':' on UNIX, ';' on MS-DOS).
+	set pathsep $::tcl_platform(pathSeparator)
+
+	set prefix ${prefix}${pathsep}
+    }
+
+    test_gdb_complete_none "$cmd ${prefix}${root}${root}/xx" \
+	"expand a non-existent filename"
+
+    test_gdb_complete_unique "$cmd ${prefix}${root}/a" \
+	"$cmd ${prefix}${root}/aaa/" "" false \
+	"expand a unique filename"
+
+    test_gdb_complete_unique "$cmd ${prefix}${root}/bb2/dir 1/uni" \
+	"$cmd ${prefix}${root}/bb2/dir 1/unique file" " " false \
+	"expand a unique filename containing whitespace"
+
+    test_gdb_complete_multiple "$cmd ${prefix}${root}/" \
+	"b" "b" {
+	    "bb1/"
+	    "bb2/"
+	} "" "" false \
+	"expand multiple directory names"
+
+    test_gdb_complete_multiple "$cmd ${prefix}${root}/" \
+	"c" "c" {
+	    "cc1/"
+	    "cc2"
+	} "" "" false \
+	"expand mixed directory and file names"
+
+    test_gdb_complete_multiple "$cmd ${prefix}${root}/aaa/" \
+	"a" "a " {
+	    "aa bb"
+	    "aa cc"
+	} "" "" false \
+	"expand filenames containing spaces"
+
+    test_gdb_complete_multiple "$cmd ${prefix}${root}/bb2/dir 2/" \
+	"fi" "le " {
+	    "file 1"
+	    "file 2"
+	} "" "" false \
+	"expand filenames containing spaces in path"
+
+    gdb_exit
+}
+
+
+# Run filename completetion tests for a sample of commands that take an
+# unquoted, unescaped filename as an argument.  Only a sample of commands
+# are (currently) tested as there's a lot of commands that accept this style
+# of filename argument.
+#
+# ROOT is the base directory as returned from setup_directory_tree, though,
+# if ROOT is a sub-directory of the user's home directory ROOT might have
+# been modified to replace the $HOME prefix with a single "~" character.
+proc run_unquoted_tests { root } {
+    # Test all the commands which allow quoting of filenames, and
+    # which require whitespace to be escaped in unquoted filenames.
+    foreach_with_prefix cmd { "maint print c-tdesc" "set logging file" \
+				  "target core" "add-auto-load-safe-path" } {
+	run_unquoted_tests_core $root $cmd
+    }
+
+    foreach prefix [list \
+			"${root}/bb2/dir 1" \
+			"${root}/bb2/dir 1/unique file" \
+			"${root}/cc1" \
+			"${root}/cc2"] {
+
+	# Don't use the full path in the test name, just use the
+	# part after the ROOT directory.
+	set id [string range $prefix [string length ${root}] end]
+	with_test_prefix "prefix=$id" {
+	    foreach_with_prefix cmd { "add-auto-load-safe-path" "path" } {
+		run_unquoted_tests_core $root $cmd $prefix
+	    }
 	}
     }
 }
 
-gdb_start
-
 set root [setup_directory_tree]
 
-run_tests $root
+run_quoting_and_escaping_tests $root
+run_unquoted_tests $root
 
 # This test relies on using the $HOME directory.  We could make this
 # work for remote hosts, but right now, this isn't supported.
@@ -114,7 +224,8 @@
 
 	with_test_prefix "with tilde" {
 	    # And rerun the tests.
-	    run_tests $tilde_root
+	    run_quoting_and_escaping_tests $tilde_root
+	    run_unquoted_tests $tilde_root
 	}
     }
 }
diff --git a/gdb/testsuite/lib/gdb.exp b/gdb/testsuite/lib/gdb.exp
index 0174aae..6c4ffc1 100644
--- a/gdb/testsuite/lib/gdb.exp
+++ b/gdb/testsuite/lib/gdb.exp
@@ -1702,6 +1702,16 @@
 
 	return $res
     }
+
+    # ::tcl_platform(pathSeparator) was added in 8.6.
+    switch $::tcl_platform(platform) {
+	windows {
+	    set ::tcl_platform(pathSeparator) ;
+	}
+	default {
+	    set ::tcl_platform(pathSeparator) :
+	}
+    }
 }
 
 if { [tcl_version_at_least 8 6 2] == 0 } {