diff --git a/src/cmd/run.go b/src/cmd/run.go
index 5ad7c30..83e6480 100644
--- a/src/cmd/run.go
+++ b/src/cmd/run.go
@@ -300,7 +300,12 @@ func runCommandWithFallbacks(container string, command []string, emitEscapeSeque
 	workDir := workingDirectory
 
 	for {
-		execArgs := constructExecArgs(container, command, detachKeysSupported, envOptions, workDir)
+		execArgs := constructExecArgs(container,
+			command,
+			detachKeysSupported,
+			envOptions,
+			fallbackToBash,
+			workDir)
 
 		if emitEscapeSequence {
 			fmt.Printf("\033]777;container;push;%s;toolbox;%s\033\\", container, currentUser.Uid)
@@ -421,8 +426,14 @@ func callFlatpakSessionHelper(container string) error {
 	return nil
 }
 
-func constructCapShArgs(command []string) []string {
-	capShArgs := []string{"capsh", "--caps=", "--", "-c", "exec \"$@\"", "bash"}
+func constructCapShArgs(command []string, useLoginShell bool) []string {
+	capShArgs := []string{"capsh", "--caps=", "--"}
+
+	if useLoginShell {
+		capShArgs = append(capShArgs, []string{"--login"}...)
+	}
+
+	capShArgs = append(capShArgs, []string{"-c", "exec \"$@\"", "bash"}...)
 	capShArgs = append(capShArgs, command...)
 
 	return capShArgs
@@ -432,6 +443,7 @@ func constructExecArgs(container string,
 	command []string,
 	detachKeysSupported bool,
 	envOptions []string,
+	fallbackToBash bool,
 	workDir string) []string {
 	var detachKeys []string
 
@@ -470,7 +482,7 @@ func constructExecArgs(container string,
 		container,
 	}...)
 
-	capShArgs := constructCapShArgs(command)
+	capShArgs := constructCapShArgs(command, !fallbackToBash)
 	execArgs = append(execArgs, capShArgs...)
 
 	return execArgs
diff --git a/test/system/104-run.bats b/test/system/104-run.bats
index 41947af..b067bad 100644
--- a/test/system/104-run.bats
+++ b/test/system/104-run.bats
@@ -13,6 +13,21 @@ teardown() {
   cleanup_containers
 }
 
+@test "run: Ensure that a login shell is used to invoke the command" {
+  create_default_container
+
+  cp "$HOME"/.bash_profile "$HOME"/.bash_profile.orig
+  echo "echo \"~/.bash_profile read\"" >>"$HOME"/.bash_profile
+
+  run $TOOLBOX run true
+
+  mv "$HOME"/.bash_profile.orig "$HOME"/.bash_profile
+
+  assert_success
+  assert_line --index 0 "~/.bash_profile read"
+  assert [ ${#lines[@]} -eq 1 ]
+}
+
 @test "run: Try to run a command in the default container with no containers created" {
   local default_container_name="$(get_system_id)-toolbox-$(get_system_version)"