diff --git a/AUTHORS b/AUTHORS
index 583fa6f9e..ab646f406 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -29,6 +29,7 @@ Benjamin Peterson
 Bernard Pratz
 Bob Ippolito
 Brian Dorsey
+Brian Maissy
 Brian Okken
 Brianna Laugher
 Bruno Oliveira
diff --git a/_pytest/debugging.py b/_pytest/debugging.py
index 23d94e688..8b5f5cc2c 100644
--- a/_pytest/debugging.py
+++ b/_pytest/debugging.py
@@ -85,6 +85,17 @@ def _enter_pdb(node, excinfo, rep):
     # for not completely clear reasons.
     tw = node.config.pluginmanager.getplugin("terminalreporter")._tw
     tw.line()
+
+    captured_stdout = rep.capstdout
+    if len(captured_stdout) > 0:
+        tw.sep(">", "captured stdout")
+        tw.line(captured_stdout)
+
+    captured_stderr = rep.capstderr
+    if len(captured_stderr) > 0:
+        tw.sep(">", "captured stderr")
+        tw.line(captured_stderr)
+
     tw.sep(">", "traceback")
     rep.toterminal(tw)
     tw.sep(">", "entering PDB")
diff --git a/changelog/3052.bugfix b/changelog/3052.bugfix
new file mode 100644
index 000000000..ea8c362a4
--- /dev/null
+++ b/changelog/3052.bugfix
@@ -0,0 +1 @@
+Added printing of captured stdout/stderr before entering pdb, and improved a test which was giving false negatives about output capturing.
diff --git a/testing/test_pdb.py b/testing/test_pdb.py
index 8618473bb..01604b633 100644
--- a/testing/test_pdb.py
+++ b/testing/test_pdb.py
@@ -141,19 +141,50 @@ class TestPDB(object):
         child.sendeof()
         self.flush(child)
 
-    def test_pdb_interaction_capture(self, testdir):
+    def test_pdb_print_captured_stdout(self, testdir):
         p1 = testdir.makepyfile("""
             def test_1():
-                print("getrekt")
+                print("get\\x20rekt")
                 assert False
         """)
         child = testdir.spawn_pytest("--pdb %s" % p1)
-        child.expect("getrekt")
+        child.expect("captured stdout")
+        child.expect("get rekt")
         child.expect("(Pdb)")
         child.sendeof()
         rest = child.read().decode("utf8")
         assert "1 failed" in rest
-        assert "getrekt" not in rest
+        assert "get rekt" not in rest
+        self.flush(child)
+
+    def test_pdb_print_captured_stderr(self, testdir):
+        p1 = testdir.makepyfile("""
+            def test_1():
+                import sys
+                sys.stderr.write("get\\x20rekt")
+                assert False
+        """)
+        child = testdir.spawn_pytest("--pdb %s" % p1)
+        child.expect("captured stderr")
+        child.expect("get rekt")
+        child.expect("(Pdb)")
+        child.sendeof()
+        rest = child.read().decode("utf8")
+        assert "1 failed" in rest
+        assert "get rekt" not in rest
+        self.flush(child)
+
+    def test_pdb_dont_print_empty_captured_stdout_and_stderr(self, testdir):
+        p1 = testdir.makepyfile("""
+            def test_1():
+                assert False
+        """)
+        child = testdir.spawn_pytest("--pdb %s" % p1)
+        child.expect("(Pdb)")
+        output = child.before.decode("utf8")
+        child.sendeof()
+        assert "captured stdout" not in output
+        assert "captured stderr" not in output
         self.flush(child)
 
     def test_pdb_interaction_exception(self, testdir):