diff --git a/buildtools/pip/pip.go b/buildtools/pip/pip.go
index 0033d7c0e2..0a53e22bd2 100644
--- a/buildtools/pip/pip.go
+++ b/buildtools/pip/pip.go
@@ -59,15 +59,18 @@ func FromFile(filename string) ([]Requirement, error) {
 
 	var reqs []Requirement
 	for _, line := range strings.Split(string(contents), "\n") {
-		trimmed := strings.TrimSpace(line)
+		// Remove all line comments and whitespace.
+		commentSplit := strings.Split(line, "#")
+		trimmed := strings.TrimSpace(commentSplit[0])
 		if strings.HasPrefix(trimmed, "#") || strings.HasPrefix(trimmed, "-") || trimmed == "" {
 			continue
 		}
+
 		log.WithField("line", line).Debug("parsing line")
 		// See https://pip.pypa.io/en/stable/reference/pip_install/#requirements-file-format
 		// and https://pip.pypa.io/en/stable/reference/pip_install/#pip-install-examples
 		matched := false
-		operators := []string{"<=", ">=", "==", ">", "<", "!="}
+		operators := []string{"===", "<=", ">=", "==", ">", "<", "!=", "~="}
 		for _, op := range operators {
 			sections := strings.Split(trimmed, op)
 			if len(sections) == 2 {
diff --git a/buildtools/pip/pip_test.go b/buildtools/pip/pip_test.go
index bfab422699..0c99409b7f 100644
--- a/buildtools/pip/pip_test.go
+++ b/buildtools/pip/pip_test.go
@@ -11,12 +11,15 @@ import (
 func TestFromFile(t *testing.T) {
 	reqs, err := pip.FromFile("testdata/requirements.txt")
 	assert.NoError(t, err)
-	assert.Equal(t, 5, len(reqs))
+	assert.Equal(t, 8, len(reqs))
 	assert.Contains(t, reqs, pip.Requirement{Name: "simple", Revision: "1.0.0", Operator: "=="})
 	assert.Contains(t, reqs, pip.Requirement{Name: "extra", Revision: "2.0.0", Operator: "=="})
 	assert.Contains(t, reqs, pip.Requirement{Name: "latest"})
 	assert.Contains(t, reqs, pip.Requirement{Name: "latestExtra"})
 	assert.Contains(t, reqs, pip.Requirement{Name: "notEqualOp", Revision: "3.0.0", Operator: ">="})
+	assert.Contains(t, reqs, pip.Requirement{Name: "comment-version", Revision: "2.0.0", Operator: "==="})
+	assert.Contains(t, reqs, pip.Requirement{Name: "comment"})
+	assert.Contains(t, reqs, pip.Requirement{Name: "tilde", Revision: "2.0.0", Operator: "~="})
 	assert.NotContains(t, reqs, pip.Requirement{Name: "-r other-requirements.txt"})
 	assert.NotContains(t, reqs, pip.Requirement{Name: "--option test-option"})
 }
diff --git a/buildtools/pip/testdata/requirements.txt b/buildtools/pip/testdata/requirements.txt
index 8319a9344b..a8042605d4 100644
--- a/buildtools/pip/testdata/requirements.txt
+++ b/buildtools/pip/testdata/requirements.txt
@@ -5,3 +5,6 @@ extra[extra]==2.0.0
 latest
 latestExtra[security]
 notEqualOp>=3.0.0
+tilde~=2.0.0
+comment-version===2.0.0 #comment
+comment #comment
\ No newline at end of file