diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.json b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.json
index 0725f864a247..d596e9294d49 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.json
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.json
@@ -11,7 +11,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test1.txt",
+          "path": ".*/test1/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -20,7 +20,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test2.txt",
+          "path": ".*/test2/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -29,7 +29,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test3.txt",
+          "path": ".*/test3/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -38,7 +38,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test4.txt",
+          "path": ".*/test4/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -46,7 +46,7 @@
         "action": "allow",
         "lifespan": "forever",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test?/file.txt",
           "permissions": [ "write" ]
         }
       }
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.sh b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.sh
index d20a679a1bf3..06bc01dd6e5e 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.sh
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_allow.sh
@@ -1,24 +1,54 @@
 #!/usr/bin/sh
 
 # A test that replying with allow forever actions previous matching prompts.
+#
+# When creating a new file is blocked on a reply to a request prompt, the
+# directory in which the file will be created is locked from other writes.
+# Thus, we can't queue up multiple outstanding writes on files in the same
+# directory. Instead, we must write files in different directories in order
+# for this test to succeed.
 
 TEST_DIR="$1"
 
-WRITABLE="$(snap run --shell prompting-client.scripted -c "cd ~; pwd")/$(basename "$TEST_DIR")"
+WRITABLE="$(snap run --shell prompting-client.scripted -c 'cd ~; pwd')/$(basename "$TEST_DIR")"
 snap run --shell prompting-client.scripted -c "mkdir -p $WRITABLE"
 
-for name in test1.txt test2.txt test3.txt ; do
+for dir in test1 test2 test3 ; do
+	mkdir -p "${TEST_DIR}/${dir}"
+	name="${dir}/file.txt"
 	echo "Attempt to write $name in the background"
-	snap run --shell prompting-client.scripted -c "echo started > ${WRITABLE}/${name}; echo $name is written > ${TEST_DIR}/${name}" &
-	timeout 10 sh -c "while ! [ -f '${WRITABLE}/${name}' ] ; do sleep 0.1 ; done"
+	snap run --shell prompting-client.scripted -c "touch ${WRITABLE}/${dir}-started; echo $name is written > ${TEST_DIR}/${name}; touch ${WRITABLE}/${dir}-finished" &
+	if ! timeout 10 sh -c "while ! [ -f '${WRITABLE}/${dir}-started' ] ; do sleep 0.1 ; done" ; then
+		echo "failed to start write of $name within timeout period"
+		exit 1
+	fi
+done
+
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has not yet finished"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test4/file.txt started"
+		exit 1
+	fi
 done
 
-echo "Attempt to write test4.txt (for which client will reply)"
-snap run --shell prompting-client.scripted -c "echo test4.txt is written > ${TEST_DIR}/test4.txt"
+echo "Attempt to write test4/file.txt (for which client will reply)"
+mkdir -p "${TEST_DIR}/test4"
+snap run --shell prompting-client.scripted -c "echo test4/file.txt is written > ${TEST_DIR}/test4/file.txt"
 
 # Wait for the client to write its result and exit
 timeout 5 sh -c 'while pgrep -f "prompting-client-scripted" > /dev/null; do sleep 0.1; done'
 
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has finished"
+	if ! [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name did not finish after client replied"
+		exit 1
+	fi
+done
+
 CLIENT_OUTPUT="$(cat "${TEST_DIR}/result")"
 
 if [ "$CLIENT_OUTPUT" != "success" ] ; then
@@ -27,7 +57,8 @@ if [ "$CLIENT_OUTPUT" != "success" ] ; then
 	exit 1
 fi
 
-for name in test1.txt test2.txt test3.txt test4.txt; do
+for dir in test1 test2 test3 test4; do
+	name="${dir}/file.txt"
 	TEST_OUTPUT="$(cat "${TEST_DIR}/${name}")"
 	if [ "$TEST_OUTPUT" != "$name is written" ] ; then
 		echo "file creation failed for $name"
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.json b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.json
index cf106ebddb4c..d05a841fb0eb 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.json
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.json
@@ -11,7 +11,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test1.txt",
+          "path": ".*/test1/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -20,7 +20,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test2.txt",
+          "path": ".*/test2/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -29,7 +29,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test3.txt",
+          "path": ".*/test3/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -38,7 +38,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test4.txt",
+          "path": ".*/test4/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -46,7 +46,7 @@
         "action": "deny",
         "lifespan": "forever",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test?/file.txt",
           "permissions": [ "write" ]
         }
       }
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.sh b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.sh
index 3782cf541018..174183588bbe 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.sh
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_actioned_by_other_pid_always_deny.sh
@@ -1,24 +1,54 @@
 #!/usr/bin/sh
 
 # A test that replying with allow forever actions previous matching prompts.
+#
+# When creating a new file is blocked on a reply to a request prompt, the
+# directory in which the file will be created is locked from other writes.
+# Thus, we can't queue up multiple outstanding writes on files in the same
+# directory. Instead, we must write files in different directories in order
+# for this test to succeed.
 
 TEST_DIR="$1"
 
-WRITABLE="$(snap run --shell prompting-client.scripted -c "cd ~; pwd")/$(basename "$TEST_DIR")"
+WRITABLE="$(snap run --shell prompting-client.scripted -c 'cd ~; pwd')/$(basename "$TEST_DIR")"
 snap run --shell prompting-client.scripted -c "mkdir -p $WRITABLE"
 
-for name in test1.txt test2.txt test3.txt ; do
+for dir in test1 test2 test3 ; do
+	mkdir -p "${TEST_DIR}/${dir}"
+	name="${dir}/file.txt"
 	echo "Attempt to write $name in the background"
-	snap run --shell prompting-client.scripted -c "echo started > ${WRITABLE}/${name}; echo $name is written > ${TEST_DIR}/${name}" &
-	timeout 10 sh -c "while ! [ -f '${WRITABLE}/${name}' ] ; do sleep 0.1 ; done"
+	snap run --shell prompting-client.scripted -c "touch ${WRITABLE}/${dir}-started; echo $name is written > ${TEST_DIR}/${name}; touch ${WRITABLE}/${dir}-finished" &
+	if ! timeout 10 sh -c "while ! [ -f '${WRITABLE}/${dir}-started' ] ; do sleep 0.1 ; done" ; then
+		echo "failed to start write of $name within timeout period"
+		exit 1
+	fi
+done
+
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has not yet finished"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test4/file.txt started"
+		exit 1
+	fi
 done
 
-echo "Attempt to write test4.txt (for which client will reply)"
-snap run --shell prompting-client.scripted -c "echo test4.txt is written > ${TEST_DIR}/test4.txt"
+echo "Attempt to write test4/file.txt (for which client will reply)"
+mkdir -p "${TEST_DIR}/test4"
+snap run --shell prompting-client.scripted -c "echo test4/file.txt is written > ${TEST_DIR}/test4/file.txt"
 
 # Wait for the client to write its result and exit
 timeout 5 sh -c 'while pgrep -f "prompting-client-scripted" > /dev/null; do sleep 0.1; done'
 
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has finished"
+	if ! [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name did not finish after client replied"
+		exit 1
+	fi
+done
+
 CLIENT_OUTPUT="$(cat "${TEST_DIR}/result")"
 
 if [ "$CLIENT_OUTPUT" != "success" ] ; then
@@ -27,7 +57,8 @@ if [ "$CLIENT_OUTPUT" != "success" ] ; then
 	exit 1
 fi
 
-for name in test1.txt test2.txt test3.txt test4.txt; do
+for dir in test1 test2 test3 test4; do
+	name="${dir}/file.txt"
 	if [ -f "${TEST_DIR}/${name}" ] ; then
 		echo "file creation unexpectedly succeeded for $name"
 		exit 1
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.json b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.json
index 23026c399a30..00da5b1d373a 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.json
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.json
@@ -11,7 +11,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test1.txt",
+          "path": ".*/test1/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -20,7 +20,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test2.txt",
+          "path": ".*/test2/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -29,7 +29,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test3.txt",
+          "path": ".*/test3/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -38,7 +38,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test4.txt",
+          "path": ".*/test4/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -46,7 +46,7 @@
         "action": "allow",
         "lifespan": "single",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test?/file.txt",
           "permissions": [ "write" ]
         }
       }
@@ -54,7 +54,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test4.txt",
+          "path": ".*/test4/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -62,7 +62,7 @@
         "action": "allow",
         "lifespan": "single",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test*/file.txt",
           "permissions": [ "write" ]
         }
       }
@@ -70,7 +70,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test5.txt",
+          "path": ".*/test5/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -78,7 +78,7 @@
         "action": "deny",
         "lifespan": "forever",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test*/file.txt",
           "permissions": [ "write" ]
         }
       }
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.sh b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.sh
index 6c909ee376a8..fad305af23a9 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.sh
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_allow.sh
@@ -1,27 +1,67 @@
 #!/usr/bin/sh
 
-# A test that replying with allow forever actions previous matching prompts.
+# A test that replying with allow once does not action previous matching prompts.
+#
+# When creating a new file is blocked on a reply to a request prompt, the
+# directory in which the file will be created is locked from other writes.
+# Thus, we can't queue up multiple outstanding writes on files in the same
+# directory. Instead, we must write files in different directories in order
+# for this test to succeed.
 
 TEST_DIR="$1"
 
-WRITABLE="$(snap run --shell prompting-client.scripted -c "cd ~; pwd")/$(basename "$TEST_DIR")"
+WRITABLE="$(snap run --shell prompting-client.scripted -c 'cd ~; pwd')/$(basename "$TEST_DIR")"
 snap run --shell prompting-client.scripted -c "mkdir -p $WRITABLE"
 
-for name in test1.txt test2.txt test3.txt ; do
+for dir in test1 test2 test3 ; do
+	mkdir -p "${TEST_DIR}/${dir}"
+	name="${dir}/file.txt"
 	echo "Attempt to write $name in the background"
-	snap run --shell prompting-client.scripted -c "echo started > ${WRITABLE}/${name}; echo $name is written > ${TEST_DIR}/${name}" &
-	timeout 10 sh -c "while ! [ -f '${WRITABLE}/${name}' ] ; do sleep 0.1 ; done"
+	snap run --shell prompting-client.scripted -c "touch ${WRITABLE}/${dir}-started; echo $name is written > ${TEST_DIR}/${name}; touch ${WRITABLE}/${dir}-finished" &
+	if ! timeout 10 sh -c "while ! [ -f '${WRITABLE}/${dir}-started' ] ; do sleep 0.1 ; done" ; then
+		echo "failed to start write of $name within timeout period"
+		exit 1
+	fi
 done
 
-echo "Attempt to write test4.txt (for which client will reply allow single)"
-snap run --shell prompting-client.scripted -c "echo test4.txt is written > ${TEST_DIR}/test4.txt"
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has not yet finished"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test4/file.txt started"
+		exit 1
+	fi
+done
+
+echo "Attempt to write test4/file.txt (for which client will reply allow single)"
+mkdir -p "${TEST_DIR}/test4"
+snap run --shell prompting-client.scripted -c "echo test4/file.txt is written > ${TEST_DIR}/test4/file.txt"
+
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name was not actioned by reply for test4/file.txt"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test5/file.txt started"
+		exit 1
+	fi
+done
 
-echo "Attempt to write test5.txt (for which client will reply deny forever)"
-snap run --shell prompting-client.scripted -c "echo test5.txt is written > ${TEST_DIR}/test5.txt"
+echo "Attempt to write test5/file.txt (for which client will reply deny forever)"
+mkdir -p "${TEST_DIR}/test5"
+snap run --shell prompting-client.scripted -c "echo test5/file.txt is written > ${TEST_DIR}/test5/file.txt"
 
 # Wait for the client to write its result and exit
 timeout 5 sh -c 'while pgrep -f "prompting-client-scripted" > /dev/null; do sleep 0.1; done'
 
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has finished"
+	if ! [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name did not finish after client replied"
+		exit 1
+	fi
+done
+
 CLIENT_OUTPUT="$(cat "${TEST_DIR}/result")"
 
 if [ "$CLIENT_OUTPUT" != "success" ] ; then
@@ -30,13 +70,14 @@ if [ "$CLIENT_OUTPUT" != "success" ] ; then
 	exit 1
 fi
 
-TEST_OUTPUT="$(cat "${TEST_DIR}/test4.txt")"
-if [ "$TEST_OUTPUT" != "test4.txt is written" ] ; then
-	echo "file creation failed for test4.txt"
+TEST_OUTPUT="$(cat "${TEST_DIR}/test4/file.txt")"
+if [ "$TEST_OUTPUT" != "test4/file.txt is written" ] ; then
+	echo "file creation failed for test4/file.txt"
 	exit 1
 fi
 
-for name in test1.txt test2.txt test3.txt test5.txt; do
+for dir in test1 test2 test3 test5; do
+	name="${dir}/file.txt"
 	if [ -f "${TEST_DIR}/${name}" ] ; then
 		echo "file creation unexpectedly succeeded for $name"
 		exit 1
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.json b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.json
index 91b814ef2d51..72d2f5cad3f6 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.json
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.json
@@ -11,7 +11,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test1.txt",
+          "path": ".*/test1/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -20,7 +20,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test2.txt",
+          "path": ".*/test2/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -29,7 +29,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test3.txt",
+          "path": ".*/test3/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -38,7 +38,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test4.txt",
+          "path": ".*/test4/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -46,7 +46,7 @@
         "action": "deny",
         "lifespan": "single",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test*/file.txt",
           "permissions": [ "write" ]
         }
       }
@@ -54,7 +54,7 @@
     {
       "prompt-filter": {
         "constraints": {
-          "path": ".*/test5.txt",
+          "path": ".*/test5/file.txt",
           "requested-permissions": [ "write" ]
         }
       },
@@ -62,7 +62,7 @@
         "action": "allow",
         "lifespan": "forever",
         "constraints": {
-          "path-pattern": "${BASE_PATH}/test*.txt",
+          "path-pattern": "${BASE_PATH}/test*/file.txt",
           "permissions": [ "write" ]
         }
       }
diff --git a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.sh b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.sh
index be6ac7a7a6d0..94ff56978fb9 100644
--- a/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.sh
+++ b/tests/main/apparmor-prompting-integration-tests/create_multiple_not_actioned_by_other_pid_single_deny.sh
@@ -1,35 +1,72 @@
 #!/usr/bin/sh
 
-# A test that replying with allow forever actions previous matching prompts.
+# A test that replying with deny once does not action previous matching prompts.
+#
+# When creating a new file is blocked on a reply to a request prompt, the
+# directory in which the file will be created is locked from other writes.
+# Thus, we can't queue up multiple outstanding writes on files in the same
+# directory. Instead, we must write files in different directories in order
+# for this test to succeed.
 
 TEST_DIR="$1"
 
-WRITABLE="$(snap run --shell prompting-client.scripted -c "cd ~; pwd")/$(basename "$TEST_DIR")"
+WRITABLE="$(snap run --shell prompting-client.scripted -c 'cd ~; pwd')/$(basename "$TEST_DIR")"
 snap run --shell prompting-client.scripted -c "mkdir -p $WRITABLE"
 
-for name in test1.txt test2.txt test3.txt ; do
+for dir in test1 test2 test3 ; do
+	mkdir -p "${TEST_DIR}/${dir}"
+	name="${dir}/file.txt"
 	echo "Attempt to write $name in the background"
-	snap run --shell prompting-client.scripted -c "echo started > ${WRITABLE}/${name}; echo $name is written > ${TEST_DIR}/${name}" &
-	timeout 10 sh -c "while ! [ -f '${WRITABLE}/${name}' ] ; do sleep 0.1 ; done"
+	snap run --shell prompting-client.scripted -c "touch ${WRITABLE}/${dir}-started; echo $name is written > ${TEST_DIR}/${name}; touch ${WRITABLE}/${dir}-finished" &
+	if ! timeout 10 sh -c "while ! [ -f '${WRITABLE}/${dir}-started' ] ; do sleep 0.1 ; done" ; then
+		echo "failed to start write of $name within timeout period"
+		exit 1
+	fi
+done
+
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has not yet finished"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test4/file.txt started"
+		exit 1
+	fi
 done
 
-echo "Attempt to write test4.txt (for which client will reply deny single)"
-snap run --shell prompting-client.scripted -c "echo test4.txt is written > ${TEST_DIR}/test4.txt"
+echo "Attempt to write test4/file.txt (for which client will reply deny single)"
+mkdir -p "${TEST_DIR}/test4"
+snap run --shell prompting-client.scripted -c "echo test4/file.txt is written > ${TEST_DIR}/test4/file.txt"
 
 echo "Check that original files have not yet been written"
-for name in test1.txt test2.txt test3.txt; do
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
 	if [ -f "${TEST_DIR}/${name}" ] ; then
 		echo "file creation unexpectedly succeeded early for $name"
 		exit 1
 	fi
+	echo "Check that write for $name was not actioned by reply for test4/file.txt"
+	if [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name finished before write for test5/file.txt started"
+		exit 1
+	fi
 done
 
-echo "Attempt to write test5.txt (for which client will reply allow forever)"
-snap run --shell prompting-client.scripted -c "echo test5.txt is written > ${TEST_DIR}/test5.txt"
+echo "Attempt to write test5/file.txt (for which client will reply allow forever)"
+mkdir -p "${TEST_DIR}/test5"
+snap run --shell prompting-client.scripted -c "echo test5/file.txt is written > ${TEST_DIR}/test5/file.txt"
 
 # Wait for the client to write its result and exit
 timeout 5 sh -c 'while pgrep -f "prompting-client-scripted" > /dev/null; do sleep 0.1; done'
 
+for dir in test1 test2 test3 ; do
+	name="${dir}/file.txt"
+	echo "Check that write for $name has finished"
+	if ! [ -f "${WRITABLE}/${dir}-finished" ] ; then
+		echo "write of $name did not finish after client replied"
+		exit 1
+	fi
+done
+
 CLIENT_OUTPUT="$(cat "${TEST_DIR}/result")"
 
 if [ "$CLIENT_OUTPUT" != "success" ] ; then
@@ -38,12 +75,13 @@ if [ "$CLIENT_OUTPUT" != "success" ] ; then
 	exit 1
 fi
 
-if [ -f "${TEST_DIR}/test4.txt" ] ; then
-	echo "file creation unexpectedly succeeded for test4.txt"
+if [ -f "${TEST_DIR}/test4/file.txt" ] ; then
+	echo "file creation unexpectedly succeeded for test4/file.txt"
 	exit 1
 fi
 
-for name in test1.txt test2.txt test3.txt test5.txt; do
+for dir in test1 test2 test3 test5; do
+	name="${dir}/file.txt"
 	TEST_OUTPUT="$(cat "${TEST_DIR}/${name}")"
 	if [ "$TEST_OUTPUT" != "$name is written" ] ; then
 		echo "file creation failed for $name"