diff --git a/src/CMakeLists.txt b/src/CMakeLists.txt
index 6c333e26d..ac717b0e5 100644
--- a/src/CMakeLists.txt
+++ b/src/CMakeLists.txt
@@ -67,6 +67,8 @@ set(SOURCES
 if (CMAKE_BUILD_TYPE MATCHES Debug)
   set(TS_DEBUG 1)
   set(DEBUG 1)
+  list(APPEND SOURCES
+    debug_guc.c)
 endif (CMAKE_BUILD_TYPE MATCHES Debug)
 
 include(build-defs.cmake)
diff --git a/src/debug_guc.c b/src/debug_guc.c
new file mode 100644
index 000000000..55ec911e7
--- /dev/null
+++ b/src/debug_guc.c
@@ -0,0 +1,215 @@
+/*
+ * This file and its contents are licensed under the Apache License 2.0.
+ * Please see the included NOTICE for copyright information and
+ * LICENSE-APACHE for a copy of the license.
+ */
+#include <postgres.h>
+#include <fmgr.h>
+#include "debug_guc.h"
+
+#include <utils/builtins.h>
+#include <utils/guc.h>
+#if PG10_GE
+#include <utils/varlena.h>
+#endif
+
+TSDLLEXPORT DebugOptimizerFlags ts_debug_optimizer_flags;
+
+enum DebugFlag
+{
+	DEBUG_FLAG_UPPER,
+	DEBUG_FLAG_REL
+};
+
+struct DebugFlagDef
+{
+	const char *name;
+	enum DebugFlag flag;
+};
+
+static struct DebugFlagDef g_flag_names[] = {
+	/* Show paths considered when planning a query. */
+	{ "show_upper_paths", DEBUG_FLAG_UPPER },
+	/* Show relations generated when planning a query. */
+	{ "show_rel_pathlist", DEBUG_FLAG_REL },
+};
+
+static unsigned long
+get_show_upper_mask(const char *paths, size_t paths_len)
+{
+	unsigned long mask = 0UL;
+	const char *beg = paths;
+
+	/* We can return early if there are no flags provided */
+	if (paths_len == 0)
+		return mask;
+
+	while (true)
+	{
+		const char *const maybe_end = strchr(beg, ',');
+		const char *const end = maybe_end == NULL ? paths + paths_len : maybe_end;
+		const size_t len = end - beg;
+		if (len > 0)
+		{
+			/* For each of the checks below, we check the provided string and
+			 * allow a prefix to the full name, so "fin" will match
+			 * "final". We have special support for "*" to denote setting all
+			 * stages. */
+			if (strncmp(beg, "*", len) == 0)
+				mask |= ~0UL;
+			else if (strncmp(beg, "setop", len) == 0)
+				mask |= STAGE_SETOP;
+#if PG11_GE
+			else if (strncmp(beg, "partial_group_agg", len) == 0)
+				mask |= STAGE_PARTIAL_GROUP_AGG;
+#endif
+			else if (strncmp(beg, "group_agg", len) == 0)
+				mask |= STAGE_GROUP_AGG;
+			else if (strncmp(beg, "window", len) == 0)
+				mask |= STAGE_WINDOW;
+			else if (strncmp(beg, "distinct", len) == 0)
+				mask |= STAGE_DISTINCT;
+			else if (strncmp(beg, "ordered", len) == 0)
+				mask |= STAGE_ORDERED;
+			else if (strncmp(beg, "final", len) == 0)
+				mask |= STAGE_FINAL;
+			else
+			{
+				char buf[20] = { 0 };
+				char *ptr;
+				strncpy(buf, beg, sizeof(buf));
+
+				/* If the path name was long, make it clear that it is
+				 * incomplete in the printout */
+				if (buf[19] != '\0')
+				{
+					buf[19] = '\0';
+					buf[18] = '.';
+					buf[17] = '.';
+					buf[16] = '.';
+				}
+
+				/* Terminate the path if it is followed by a comma */
+				ptr = strchr(buf, ',');
+				if (ptr)
+					*ptr = '\0';
+
+				ereport(ERROR,
+						(errcode(ERRCODE_INVALID_PARAMETER_VALUE),
+						 errmsg_internal("unrecognized flag option \"%s\"", buf)));
+			}
+		}
+		if (maybe_end == NULL)
+			break;
+		beg = maybe_end + 1;
+	}
+	return mask;
+}
+
+static bool
+set_debug_flag(const char *flag_string, size_t length, DebugOptimizerFlags *flags)
+{
+	int i;
+	char *end;
+	size_t flag_length;
+
+	if ((end = strchr(flag_string, '=')) != NULL)
+	{
+		Assert(end - flag_string >= 0);
+		flag_length = end - flag_string;
+	}
+	else
+	{
+		flag_length = length;
+	}
+
+	for (i = 0; i < sizeof(g_flag_names) / sizeof(*g_flag_names); ++i)
+		if (strncmp(g_flag_names[i].name, flag_string, flag_length) == 0)
+			switch (g_flag_names[i].flag)
+			{
+				case DEBUG_FLAG_UPPER:
+					flags->show_upper = get_show_upper_mask(end + 1, length - flag_length - 1);
+					return true;
+				case DEBUG_FLAG_REL:
+					flags->show_rel = true;
+					return true;
+			}
+	return false;
+}
+
+static bool
+parse_optimizer_flags(const char *string, DebugOptimizerFlags *flags)
+{
+	char *rawname;
+	List *namelist;
+	ListCell *cell;
+
+	Assert(string && flags);
+
+	if (strlen(string) == 0)
+		return true;
+
+	rawname = pstrdup(string);
+	if (!SplitIdentifierString(rawname, ':', &namelist))
+	{
+		GUC_check_errdetail("Invalid flag string syntax.");
+		GUC_check_errhint("The flags string should be a list of colon-separated identifiers.");
+		pfree(rawname);
+		list_free(namelist);
+		return false;
+	}
+
+	foreach (cell, namelist)
+	{
+		char *flag_string = (char *) lfirst(cell);
+		if (!set_debug_flag(flag_string, strlen(flag_string), flags))
+		{
+			GUC_check_errdetail("Unrecognized flag setting \"%s\".", flag_string);
+			GUC_check_errhint("Allowed values are: show_upper_paths show_rel_pathlist");
+			pfree(rawname);
+			list_free(namelist);
+			return false;
+		}
+	}
+
+	pfree(rawname);
+	list_free(namelist);
+	return true;
+}
+
+static bool
+debug_optimizer_flags_check(char **newval, void **extra, GucSource source)
+{
+	DebugOptimizerFlags flags;
+
+	Assert(newval);
+
+	if (*newval)
+		return parse_optimizer_flags(*newval, &flags);
+	return true;
+}
+
+static void
+debug_optimizer_flags_assign(const char *newval, void *extra)
+{
+	if (newval && !parse_optimizer_flags(newval, &ts_debug_optimizer_flags))
+		ereport(ERROR,
+				(errcode(ERRCODE_INTERNAL_ERROR),
+				 errmsg("cannot parse \"%s\" as debug optimizer flags", newval)));
+}
+
+void
+ts_debug_init(void)
+{
+	static char *debug_optimizer_flags_string = NULL;
+	DefineCustomStringVariable("timescaledb.debug_optimizer_flags",
+							   "List of optimizer debug flags",
+							   "A list of flags for configuring the optimizer debug output.",
+							   &debug_optimizer_flags_string,
+							   NULL,
+							   PGC_USERSET,
+							   GUC_LIST_INPUT,
+							   /* check_hook= */ debug_optimizer_flags_check,
+							   /* assign_hook= */ debug_optimizer_flags_assign,
+							   /* show_hook= */ NULL);
+}
diff --git a/src/debug_guc.h b/src/debug_guc.h
new file mode 100644
index 000000000..3c55f9f60
--- /dev/null
+++ b/src/debug_guc.h
@@ -0,0 +1,50 @@
+/*
+ * This file and its contents are licensed under the Apache License 2.0.
+ * Please see the included NOTICE for copyright information and
+ * LICENSE-APACHE for a copy of the license.
+ */
+#ifndef TIMESCALEDB_DEBUG_GUC_H
+#define TIMESCALEDB_DEBUG_GUC_H
+
+#include <postgres.h>
+#include <fmgr.h>
+#include <utils/guc.h>
+
+#include "compat.h"
+#include "export.h"
+
+/*
+ * Enable printout inside ts_create_upper based on the stage provided. It is
+ * possible to enable printout for multiple stages, so we take the existing
+ * stage list and create a mask from it.
+ */
+#define STAGE_SETOP (1UL << UPPERREL_SETOP) /* Enabled using "setop" */
+#if PG11_GE
+#define STAGE_PARTIAL_GROUP_AGG                                                                    \
+	(1UL << UPPERREL_PARTIAL_GROUP_AGG) /* Enabled using "partial_group_agg" */
+#endif
+#define STAGE_GROUP_AGG (1UL << UPPERREL_GROUP_AGG) /* Enabled using "group_agg" */
+#define STAGE_WINDOW (1UL << UPPERREL_WINDOW)		/* Enabled using "window" */
+#define STAGE_DISTINCT (1UL << UPPERREL_DISTINCT)   /* Enabled using "distinct" */
+#define STAGE_ORDERED (1UL << UPPERREL_ORDERED)		/* Enabled using "ordered" */
+#define STAGE_FINAL (1UL << UPPERREL_FINAL)			/* Enabled using "final" */
+
+/*
+ * Debug flags for the optimizer.
+ *
+ * Add new flags here as you see fit, but don't forget to update the flag list
+ * `flag_names` in guc.c.
+ */
+typedef struct DebugOptimizerFlags
+{
+	/* Bit mask to represent set of UpperRelationKind, which is used as the
+	 * stage inside create_upper. */
+	unsigned long show_upper;
+	bool show_rel;
+} DebugOptimizerFlags;
+
+extern TSDLLEXPORT DebugOptimizerFlags ts_debug_optimizer_flags;
+
+extern void ts_debug_init(void);
+
+#endif /* TIMESCALEDB_DEBUG_GUC_H */
diff --git a/src/init.c b/src/init.c
index f06c83ca6..be5304393 100644
--- a/src/init.c
+++ b/src/init.c
@@ -14,6 +14,7 @@
 #include "extension.h"
 #include "bgw/launcher_interface.h"
 #include "guc.h"
+#include "debug_guc.h"
 #include "catalog.h"
 #include "version.h"
 #include "compat.h"
@@ -89,6 +90,7 @@ _PG_init(void)
 #endif
 #ifdef TS_DEBUG
 	_conn_mock_init();
+	ts_debug_init();
 #endif
 }
 
diff --git a/test/expected/guc_options.out b/test/expected/guc_options.out
new file mode 100644
index 000000000..b0badf3df
--- /dev/null
+++ b/test/expected/guc_options.out
@@ -0,0 +1,111 @@
+-- This file and its contents are licensed under the Apache License 2.0.
+-- Please see the included NOTICE for copyright information and
+-- LICENSE-APACHE for a copy of the license.
+\c :TEST_DBNAME :ROLE_SUPERUSER
+SET timescaledb.debug_optimizer_flags = '';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ 
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=final';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=final
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=fin
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin,win';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=fin,win
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=*,fin,win';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=*,fin,win
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=*';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=*
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=win:show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=win:show_rel
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = '"show_upper=win":show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ "show_upper=win":show_rel
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_upper=win : show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_upper=win : show_rel
+(1 row)
+
+SET timescaledb.debug_optimizer_flags = 'show_rel:show_upper=win';
+SHOW timescaledb.debug_optimizer_flags;
+ timescaledb.debug_optimizer_flags 
+-----------------------------------
+ show_rel:show_upper=win
+(1 row)
+
+-- These should all fail
+\set ON_ERROR_STOP 0
+SET timescaledb.debug_optimizer_flags = NULL;
+ERROR:  syntax error at or near "NULL" at character 41
+SET timescaledb.debug_optimizer_flags = 'invalid';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": "invalid"
+SET timescaledb.debug_optimizer_flags = '"unmatched quote:';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": ""unmatched quote:"
+SET timescaledb.debug_optimizer_flags = 'space between';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": "space between"
+SET timescaledb.debug_optimizer_flags = 'space between:';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": "space between:"
+SET timescaledb.debug_optimizer_flags = 'show_rel:invalid';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": "show_rel:invalid"
+SET timescaledb.debug_optimizer_flags = 'invalid:show_rel';
+ERROR:  invalid value for parameter "timescaledb.debug_optimizer_flags": "invalid:show_rel"
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin,xxx';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,fin';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=win,xxx,fin';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=*,xxx';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,*';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,*,yyy';
+ERROR:  unrecognized flag option "xxx"
+SET timescaledb.debug_optimizer_flags = 'show_upper=supercalifragilisticexpialidochious';
+ERROR:  unrecognized flag option "supercalifragili..."
+SET timescaledb.debug_optimizer_flags = 'show_upper=super,califragilisticexpialidochious';
+ERROR:  unrecognized flag option "super"
+\set ON_ERROR_STOP 1
diff --git a/test/sql/CMakeLists.txt b/test/sql/CMakeLists.txt
index e9d8174d2..add763efe 100644
--- a/test/sql/CMakeLists.txt
+++ b/test/sql/CMakeLists.txt
@@ -79,6 +79,7 @@ if (CMAKE_BUILD_TYPE MATCHES Debug)
     bgw_launcher.sql
     bgw_db_scheduler.sql
     c_unit_tests.sql
+    guc_options.sql
     loader.sql
     metadata.sql
     net.sql
diff --git a/test/sql/guc_options.sql b/test/sql/guc_options.sql
new file mode 100644
index 000000000..005620c5c
--- /dev/null
+++ b/test/sql/guc_options.sql
@@ -0,0 +1,46 @@
+-- This file and its contents are licensed under the Apache License 2.0.
+-- Please see the included NOTICE for copyright information and
+-- LICENSE-APACHE for a copy of the license.
+
+\c :TEST_DBNAME :ROLE_SUPERUSER
+SET timescaledb.debug_optimizer_flags = '';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=final';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin,win';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=*,fin,win';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=*';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=win:show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = '"show_upper=win":show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_upper=win : show_rel';
+SHOW timescaledb.debug_optimizer_flags;
+SET timescaledb.debug_optimizer_flags = 'show_rel:show_upper=win';
+SHOW timescaledb.debug_optimizer_flags;
+
+-- These should all fail
+\set ON_ERROR_STOP 0
+SET timescaledb.debug_optimizer_flags = NULL;
+SET timescaledb.debug_optimizer_flags = 'invalid';
+SET timescaledb.debug_optimizer_flags = '"unmatched quote:';
+SET timescaledb.debug_optimizer_flags = 'space between';
+SET timescaledb.debug_optimizer_flags = 'space between:';
+SET timescaledb.debug_optimizer_flags = 'show_rel:invalid';
+SET timescaledb.debug_optimizer_flags = 'invalid:show_rel';
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx';
+SET timescaledb.debug_optimizer_flags = 'show_upper=fin,xxx';
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,fin';
+SET timescaledb.debug_optimizer_flags = 'show_upper=win,xxx,fin';
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx';
+SET timescaledb.debug_optimizer_flags = 'show_upper=*,xxx';
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,*';
+SET timescaledb.debug_optimizer_flags = 'show_upper=xxx,*,yyy';
+SET timescaledb.debug_optimizer_flags = 'show_upper=supercalifragilisticexpialidochious';
+SET timescaledb.debug_optimizer_flags = 'show_upper=super,califragilisticexpialidochious';
+\set ON_ERROR_STOP 1