diff --git a/tests/try/plan-env-file/data/.fmf/version b/tests/try/plan-env-file/data/.fmf/version
new file mode 100644
index 0000000000..d00491fd7e
--- /dev/null
+++ b/tests/try/plan-env-file/data/.fmf/version
@@ -0,0 +1 @@
+1
diff --git a/tests/try/plan-env-file/data/plan.fmf b/tests/try/plan-env-file/data/plan.fmf
new file mode 100644
index 0000000000..eaf75558c6
--- /dev/null
+++ b/tests/try/plan-env-file/data/plan.fmf
@@ -0,0 +1,13 @@
+summary: Telling how it is
+discover:
+    how: fmf
+provision:
+    how: local
+prepare:
+    how: shell
+    script: echo "MY_VAR=good" >> $TMT_PLAN_ENVIRONMENT_FILE
+execute:
+    how: tmt
+finish:
+    how: shell
+    script: echo "and yours is $YOUR_VAR..."  # Check if env-file sourced after execute
diff --git a/tests/try/plan-env-file/data/start_ask_manual.exp b/tests/try/plan-env-file/data/start_ask_manual.exp
new file mode 100755
index 0000000000..5d95673103
--- /dev/null
+++ b/tests/try/plan-env-file/data/start_ask_manual.exp
@@ -0,0 +1,23 @@
+#!/usr/bin/expect -f
+# Run all the steps manually and quit
+
+spawn tmt try -a -p /plan
+
+expect "What do we do next?"
+send -- "d\r"
+
+expect "What do we do next?"
+send -- "p\r"
+
+expect "What do we do next?"
+send -- "e\r"
+
+expect "What do we do next?"
+send -- "r\r"
+
+expect "What do we do next?"
+send -- "f\r"
+
+expect "What do we do next?"
+send -- "q\r"
+expect eof
diff --git a/tests/try/plan-env-file/data/start_ask_test.exp b/tests/try/plan-env-file/data/start_ask_test.exp
new file mode 100755
index 0000000000..f22f9def6a
--- /dev/null
+++ b/tests/try/plan-env-file/data/start_ask_test.exp
@@ -0,0 +1,14 @@
+#!/usr/bin/expect -f
+# Run the prepare step, start the test and quit
+
+spawn tmt try -a -p /plan
+
+expect "What do we do next?"
+send -- "p\r"
+
+expect "What do we do next?"
+send -- "t\r"
+
+expect "What do we do next?"
+send -- "q\r"
+expect eof
diff --git a/tests/try/plan-env-file/data/start_ask_test_skip.exp b/tests/try/plan-env-file/data/start_ask_test_skip.exp
new file mode 100755
index 0000000000..80fc195a1b
--- /dev/null
+++ b/tests/try/plan-env-file/data/start_ask_test_skip.exp
@@ -0,0 +1,11 @@
+#!/usr/bin/expect -f
+# Skip the prepare step, start the test and quit
+
+spawn tmt try -a -p /plan
+
+expect "What do we do next?"
+send -- "t\r"
+
+expect "What do we do next?"
+send -- "q\r"
+expect eof
diff --git a/tests/try/plan-env-file/data/start_login.exp b/tests/try/plan-env-file/data/start_login.exp
new file mode 100755
index 0000000000..6f448cc61b
--- /dev/null
+++ b/tests/try/plan-env-file/data/start_login.exp
@@ -0,0 +1,18 @@
+#!/usr/bin/expect -f
+# Login to guest, run the test and quit
+
+# ord('D') % 32
+set ctrlD \x04
+
+spawn tmt try -l -p /plan
+
+expect "Starting interactive shell"
+sleep 3
+send -- $ctrlD
+
+expect "What do we do next?"
+send -- "t\r"
+
+expect "What do we do next?"
+send -- "q\r"
+expect eof
diff --git a/tests/try/plan-env-file/data/start_test.exp b/tests/try/plan-env-file/data/start_test.exp
new file mode 100755
index 0000000000..998cd383ce
--- /dev/null
+++ b/tests/try/plan-env-file/data/start_test.exp
@@ -0,0 +1,8 @@
+#!/usr/bin/expect -f
+# Try the plan and quit
+
+spawn tmt try -p /plan
+
+expect "What do we do next?"
+send -- "q\r"
+expect eof
diff --git a/tests/try/plan-env-file/data/test.fmf b/tests/try/plan-env-file/data/test.fmf
new file mode 100644
index 0000000000..07ccfc7c05
--- /dev/null
+++ b/tests/try/plan-env-file/data/test.fmf
@@ -0,0 +1,5 @@
+summary: How it is
+framework: shell
+test: |
+    echo "My variable is $MY_VAR..."  # Check whether plan-file sourced after prepare
+    echo "YOUR_VAR=bad" >> $TMT_PLAN_ENVIRONMENT_FILE  # Variable to source after execute
diff --git a/tests/try/plan-env-file/main.fmf b/tests/try/plan-env-file/main.fmf
new file mode 100644
index 0000000000..633094eb9a
--- /dev/null
+++ b/tests/try/plan-env-file/main.fmf
@@ -0,0 +1,5 @@
+summary: Verify plan environment file gets sourced
+description:
+    Check that environment file inside TMT_PLAN_ENVIRONMENT_FILE are
+    sourced after prepare and execute steps when running tmt try.
+
diff --git a/tests/try/plan-env-file/test.sh b/tests/try/plan-env-file/test.sh
new file mode 100755
index 0000000000..53ba4a4c0c
--- /dev/null
+++ b/tests/try/plan-env-file/test.sh
@@ -0,0 +1,44 @@
+#!/bin/bash
+. /usr/share/beakerlib/beakerlib.sh || exit 1
+rlJournalStart
+    rlPhaseStartSetup
+        rlRun "tmp=\$(mktemp -d)" 0 "Create tmp directory"
+        rlRun "export TMT_NO_COLOR=1"
+        rlRun "pushd data"
+    rlPhaseEnd
+
+    rlPhaseStartTest "Try the plan and quit"
+        rlRun -s "LANG=en_US ./start_test.exp" 0
+        rlAssertGrep "My variable is good" $rlRun_LOG
+        rlAssertGrep "and yours is bad" $rlRun_LOG
+    rlPhaseEnd
+
+    rlPhaseStartTest "Run the prepare step, start the test and quit"
+        rlRun -s "LANG=en_US ./start_ask_test.exp" 0
+        rlAssertGrep "My variable is good" $rlRun_LOG
+        rlAssertGrep "and yours is bad" $rlRun_LOG
+    rlPhaseEnd
+
+    rlPhaseStartTest "Login to guest, run the test and quit"
+        rlRun -s "LANG=en_US ./start_login.exp" 0
+        rlAssertGrep "My variable is good" $rlRun_LOG
+        rlAssertGrep "and yours is bad" $rlRun_LOG
+    rlPhaseEnd
+
+    rlPhaseStartTest "Run all the steps manually and quit"
+        rlRun -s "LANG=en_US ./start_ask_manual.exp" 0
+        rlAssertGrep "My variable is good" $rlRun_LOG
+        rlAssertGrep "and yours is bad" $rlRun_LOG
+    rlPhaseEnd
+
+    rlPhaseStartTest "Skip the prepare step, start the test and quit"
+        rlRun -s "LANG=en_US ./start_ask_test_skip.exp" 0
+        rlAssertNotGrep "My variable is good" $rlRun_LOG
+        rlAssertGrep "and yours is bad" $rlRun_LOG
+    rlPhaseEnd
+
+    rlPhaseStartCleanup
+        rlRun "popd"
+        rlRun "rm -r $tmp" 0 "Remove tmp directory"
+    rlPhaseEnd
+rlJournalEnd
diff --git a/tmt/trying.py b/tmt/trying.py
index e0f7f9b484..70e198c203 100644
--- a/tmt/trying.py
+++ b/tmt/trying.py
@@ -293,15 +293,15 @@ def action_start_test(self, plan: Plan) -> None:
 
         plan.discover.go()
         plan.provision.go()
-        plan.prepare.go()
-        plan.execute.go()
+        self.action_prepare(plan)
+        self.action_execute(plan)
 
     def action_start_login(self, plan: Plan) -> None:
         """ Start with login """
         self.action_start(plan)
 
         plan.provision.go()
-        plan.prepare.go()
+        self.action_prepare(plan)
         assert plan.login is not None  # Narrow type
         plan.login.go(force=True)
 
@@ -314,7 +314,7 @@ def action_start_ask(self, plan: Plan) -> None:
     def action_test(self, plan: Plan) -> None:
         """ Test again """
         plan.discover.go(force=True)
-        plan.execute.go(force=True)
+        self.action_execute(plan)
 
     def action_login(self, plan: Plan) -> None:
         """ Log into the guest """
@@ -373,10 +373,12 @@ def action_discover(self, plan: Plan) -> None:
     def action_prepare(self, plan: Plan) -> None:
         """ Prepare the guest """
         plan.prepare.go(force=True)
+        plan._source_plan_environment_file()
 
     def action_execute(self, plan: Plan) -> None:
         """ Execute tests """
         plan.execute.go(force=True)
+        plan._source_plan_environment_file()
 
     def action_report(self, plan: Plan) -> None:
         """ Report results """