diff --git a/tests/history.expect b/tests/history.expect
deleted file mode 100644
index 8c896688d..000000000
--- a/tests/history.expect
+++ /dev/null
@@ -1,167 +0,0 @@
-# vim: set filetype=expect:
-#
-# This is a very fragile test. Sorry about that. But interactively entering
-# commands and verifying they are recorded correctly in the interactive
-# history and that history can be manipulated is inherently difficult.
-#
-# This is meant to verify just a few of the most basic behaviors of the
-# interactive history to hopefully keep regressions from happening. It is not
-# meant to be a comprehensive test of the history subsystem. Those types of
-# tests belong in the src/fish_tests.cpp module.
-#
-
-# The history function might pipe output through the user's pager. We don't
-# want something like `less` to complicate matters so force the use of `cat`.
-set ::env(PAGER) cat
-spawn $fish
-expect_prompt
-
-# ==========
-# Start by ensuring we're not affected by earlier tests. Clear the history.
-send "builtin history clear\r"
-expect_prompt
-
-# ==========
-# The following tests verify the behavior of the history builtin.
-# ==========
-
-# ==========
-# List our history which should be empty after just clearing it.
-send "echo start1; builtin history; echo end1\r"
-expect_prompt -re {start1\r\nend1\r\n} {
-    puts "empty history detected as expected"
-} timeout {
-    puts stderr "empty history not detected as expected"
-}
-
-# ==========
-# Our history should now contain the previous command and nothing else.
-send "echo start2; builtin history; echo end2\r"
-expect_prompt -re {start2\r\necho start1; builtin history; echo end1\r\nend2\r\n} {
-    puts "first history command detected as expected"
-} timeout {
-    puts stderr "first history command not detected as expected"
-}
-
-# ==========
-# The following tests verify the behavior of the history function.
-# ==========
-
-# ==========
-# Verify explicit searching for the first two commands in the previous tests
-# returns the expected results.
-send "history search --reverse 'echo start' | cat\r"
-expect_prompt -re {\r\necho start1;.*\r\necho start2;} {
-    puts "history function explicit search succeeded"
-} timeout {
-    puts stderr "history function explicit search failed"
-}
-
-# ==========
-# Verify searching is the implicit action.
-send "history -p 'echo start'\r"
-expect_prompt -re {\r\necho start2.*\r\necho start1} {
-    puts "history function implicit search succeeded"
-} timeout {
-    puts stderr "history function implicit search failed"
-}
-
-# ==========
-# Verify searching with a request for timestamps includes the timestamps.
-send "history search --show-time='# %F %T%n' --prefix 'echo start'\r"
-expect_prompt -re {\r\n# \d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d\r\necho start2; .*\r\n# \d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d\r\necho start1; } {
-    puts "history function implicit search with timestamps succeeded"
-} timeout {
-    puts stderr "history function implicit search with timestamps failed"
-}
-
-# ==========
-# Verify explicit searching for an exact command returns just that command.
-# returns the expected results.
-send "echo hello\r"
-expect_prompt
-send "echo goodbye\r"
-expect_prompt
-send "echo hello again\r"
-expect_prompt
-send "echo hello AGAIN\r"
-expect_prompt
-
-send "history search --exact 'echo goodbye' | cat\r"
-expect_prompt -re {\r\necho goodbye\r\n} {
-    puts "history function explicit exact search 'echo goodbye' succeeded"
-} timeout {
-    puts stderr "history function explicit exact search 'echo goodbye' failed"
-}
-
-send "history search --exact 'echo hello' | cat\r"
-expect_prompt -re {\r\necho hello\r\n} {
-    puts "history function explicit exact search 'echo hello' succeeded"
-} timeout {
-    puts stderr "history function explicit exact search 'echo hello' failed"
-}
-
-# This is slightly subtle in that it shouldn't actually match anything between
-# the command we sent and the next prompt.
-send "history search --exact 'echo hell' | cat\r"
-expect_prompt -re {history search --exact 'echo hell' | cat\r\n} {
-    puts "history function explicit exact search 'echo hell' succeeded"
-} timeout {
-    puts stderr "history function explicit exact search 'echo hell' failed"
-}
-
-# Verify that glob searching works.
-send "history search --prefix 'echo start*echo end' | cat\r"
-expect_prompt -re {echo start1; builtin history; echo end1\r\n} {
-    puts "history function explicit glob search 'echo start*echo end' succeeded"
-} timeout {
-    puts stderr "history function explicit glob search 'echo start*echo end' failed"
-}
-
-# ==========
-# Delete a single command we recently ran.
-send "history delete -e -C 'echo hello'\r"
-expect -re {history delete -e -C 'echo hello'\r\n}
-send "echo count hello (history search -e -C 'echo hello' | wc -l | string trim)\r"
-expect -re {\r\ncount hello 0\r\n} {
-    puts "history function explicit exact delete 'echo hello' succeeded"
-} timeout {
-    puts stderr "history function explicit exact delete 'echo hello' failed"
-}
-
-# ==========
-# Interactively delete one of multiple matched commands. This verifies that we
-# delete the first entry matched by the prefix search (the most recent command
-# sent above that matches).
-send "history delete -p 'echo hello'\r"
-expect -re {history delete -p 'echo hello'\r\n}
-expect -re {\[1\] echo hello AGAIN\r\n}
-expect -re {\[2\] echo hello again\r\n\r\n}
-expect -re {Enter nothing to cancel.*\r\nEnter "all" to delete all the matching entries\.\r\n}
-expect -re {Delete which entries\? >}
-send "1\r"
-expect -re {Deleting history entry 1: "echo hello AGAIN"\r\n}
-
-# Verify that the deleted history entry is gone and the other one that matched
-# the prefix search above is still there.
-send "echo count AGAIN (history search -e -C 'echo hello AGAIN' | wc -l | string trim)\r"
-expect -re {\r\ncount AGAIN 0\r\n} {
-    puts "history function explicit prefix delete 'echo hello AGAIN' succeeded"
-} timeout {
-    puts stderr "history function explicit prefix delete 'echo hello AGAIN' failed"
-}
-
-send "echo count again (history search -e -C 'echo hello again' | wc -l | string trim)\r"
-expect -re {\r\ncount again 1\r\n} {
-    puts "history function explicit exact search 'echo hello again' succeeded"
-} timeout {
-    puts stderr "history function explicit exact search 'echo hello again' failed"
-}
-
-# Verify that the $history var has the expected content.
-send "echo history2=\$history\[2\]\r"
-expect -re {\r\nhistory2=echo count AGAIN .*\r\n} {
-    puts "history\[2\] had the correct data"
-} timeout {
-    puts stderr "history\[2\] had the wrong data"
-}
diff --git a/tests/history.expect.err b/tests/history.expect.err
deleted file mode 100644
index e69de29bb..000000000
diff --git a/tests/history.expect.out b/tests/history.expect.out
deleted file mode 100644
index c4eb84d75..000000000
--- a/tests/history.expect.out
+++ /dev/null
@@ -1,13 +0,0 @@
-empty history detected as expected
-first history command detected as expected
-history function explicit search succeeded
-history function implicit search succeeded
-history function implicit search with timestamps succeeded
-history function explicit exact search 'echo goodbye' succeeded
-history function explicit exact search 'echo hello' succeeded
-history function explicit exact search 'echo hell' succeeded
-history function explicit glob search 'echo start*echo end' succeeded
-history function explicit exact delete 'echo hello' succeeded
-history function explicit prefix delete 'echo hello AGAIN' succeeded
-history function explicit exact search 'echo hello again' succeeded
-history[2] had the correct data
diff --git a/tests/pexpects/history.py b/tests/pexpects/history.py
new file mode 100644
index 000000000..196be9850
--- /dev/null
+++ b/tests/pexpects/history.py
@@ -0,0 +1,127 @@
+#!/usr/bin/env python3
+# This is a very fragile test. Sorry about that. But interactively entering
+# commands and verifying they are recorded correctly in the interactive
+# history and that history can be manipulated is inherently difficult.
+#
+# This is meant to verify just a few of the most basic behaviors of the
+# interactive history to hopefully keep regressions from happening. It is not
+# meant to be a comprehensive test of the history subsystem. Those types of
+# tests belong in the src/fish_tests.cpp module.
+#
+
+# The history function might pipe output through the user's pager. We don't
+# want something like `less` to complicate matters so force the use of `cat`.
+from pexpect_helper import SpawnedProc
+import os
+
+os.environ["PAGER"] = "cat"
+os.environ["TERM"] = "xterm"
+
+sp = SpawnedProc(env=os.environ.copy())
+
+send, sendline, sleep, expect_prompt, expect_re, expect_str = (
+    sp.send,
+    sp.sendline,
+    sp.sleep,
+    sp.expect_prompt,
+    sp.expect_re,
+    sp.expect_str,
+)
+expect_prompt()
+
+# ==========
+# Start by ensuring we're not affected by earlier tests. Clear the history.
+sendline("builtin history clear")
+expect_prompt()
+
+# ==========
+# The following tests verify the behavior of the history builtin.
+# ==========
+
+# ==========
+# List our history which should be empty after just clearing it.
+sendline("echo start1; builtin history; echo end1")
+expect_prompt("start1\r\nend1\r\n")
+
+# Our history should now contain the previous command and nothing else.
+sendline("echo start2; builtin history; echo end2")
+expect_prompt("start2\r\necho start1; builtin history; echo end1\r\nend2\r\n")
+
+# ==========
+# The following tests verify the behavior of the history function.
+# ==========
+
+# ==========
+# Verify explicit searching for the first two commands in the previous tests
+# returns the expected results.
+sendline("history search --reverse 'echo start' | cat")
+expect_prompt("echo start1;.*\r\necho start2;")
+
+# ==========
+# Verify searching is the implicit action.
+sendline("history -p 'echo start'")
+expect_prompt("echo start2.*\r\necho start1")
+
+# ==========
+# Verify searching with a request for timestamps includes the timestamps.
+sendline("history search --show-time='# %F %T%n' --prefix 'echo start'")
+expect_prompt("# \d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d\r\necho start2; .*\r\n# \d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d\r\necho start1;")
+
+# ==========
+# Verify explicit searching for an exact command returns just that command.
+# returns the expected results.
+sendline("echo hello")
+expect_prompt()
+sendline("echo goodbye")
+expect_prompt()
+sendline("echo hello again")
+expect_prompt()
+sendline("echo hello AGAIN")
+expect_prompt()
+
+sendline("history search --exact 'echo goodbye' | cat")
+expect_prompt("echo goodbye\r\n")
+
+sendline("history search --exact 'echo hello' | cat")
+expect_prompt("echo hello\r\n")
+
+# This is slightly subtle in that it shouldn't actually match anything between
+# the command we sent and the next prompt.
+sendline("history search --exact 'echo hell' | cat")
+expect_prompt("history search --exact 'echo hell' | cat\r\n")
+
+# Verify that glob searching works.
+sendline("history search --prefix 'echo start*echo end' | cat")
+expect_prompt("echo start1; builtin history; echo end1\r\n")
+
+# ==========
+# Delete a single command we recently ran.
+sendline("history delete -e -C 'echo hello'")
+expect_str("history delete -e -C 'echo hello'\r\n")
+sendline("echo count hello (history search -e -C 'echo hello' | wc -l | string trim)")
+expect_re("count hello 0\r\n")
+
+# ==========
+# Interactively delete one of multiple matched commands. This verifies that we
+# delete the first entry matched by the prefix search (the most recent command
+# sent above that matches).
+sendline("history delete -p 'echo hello'")
+expect_re("history delete -p 'echo hello'\r\n")
+expect_re("\[1\] echo hello AGAIN\r\n")
+expect_re("\[2\] echo hello again\r\n\r\n")
+expect_re('Enter nothing to cancel.*\r\nEnter "all" to delete all the matching entries\.\r\n')
+expect_re("Delete which entries\? >")
+sendline("1")
+expect_re('Deleting history entry 1: "echo hello AGAIN"\r\n')
+
+# Verify that the deleted history entry is gone and the other one that matched
+# the prefix search above is still there.
+sendline("echo count AGAIN (history search -e -C 'echo hello AGAIN' | wc -l | string trim)")
+expect_re("count AGAIN 0\r\n")
+
+sendline("echo count again (history search -e -C 'echo hello again' | wc -l | string trim)")
+expect_re("count again 1\r\n")
+
+# Verify that the $history var has the expected content.
+sendline("echo history2=$history\[2\]")
+expect_re("history2=echo count AGAIN .*\r\n")