diff --git a/CHANGELOG.md b/CHANGELOG.md
index fdc2634..7f0a360 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,6 +9,12 @@ This project uses [Semantic Versioning](https://semver.org).
 
 ### Added
 
+- **`rules:if:` expression evaluator improvements** — four correctness fixes to the GitLab CI expression parser:
+  - **Multi-line expressions** — newlines (`\n`, `\r`) are now treated as whitespace between tokens, so block-scalar `if:` values (e.g. `if: | ...`) and folded YAML scalars with `||`/`&&` on a continuation line are parsed correctly instead of falling back to permissive `true`.
+  - **`${VAR}` curly-brace variable syntax** — `${CI_COMMIT_BRANCH}` is now equivalent to `$CI_COMMIT_BRANCH` everywhere a value is expected.
+  - **Regex flags** — `/pattern/i`, `/pattern/m`, `/pattern/s` are now honoured; the `i` flag (case-insensitive) is translated to Go's `(?i)` prefix before compiling. Unknown flags are silently ignored.
+  - **Variable as regex RHS** — `$BRANCH =~ $PATTERN` where `$PATTERN` holds a `/regex/[flags]` string is now evaluated by extracting and compiling the pattern from the variable's value; if the value is empty or does not look like a regex literal the expression falls back to permissive `true`.
+
 - **File and line numbers on findings** — every finding now includes the source file and line where the job is defined, e.g. `[ERROR] job "deploy" (src/deploy.yml:14): …`. For jobs that come from local or fetched includes the file reflects the include source. Pipeline-level findings (workflow rules, missing stages) reference the root pipeline file.
 
 - **`glint graph includes` shows jobs per file** — each node in the Mermaid include dependency graph now shows the jobs defined directly in that file. Jobs are rendered as rounded nodes (`(name)`) in a distinct light-purple style, connected with dashed arrows (`-.->`) to distinguish ownership from the include hierarchy (solid `-->` arrows). The root pipeline file always shows its direct jobs; local and fetched project/component nodes show theirs when the file can be read.
diff --git a/Taskfile.yml b/Taskfile.yml
index fb0253c..d07f431 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -59,6 +59,12 @@ tasks:
         ignore_error: false
       - cmd: ./{{.BINARY}} check --tag v1.0.0 testdata/context_rules.yml
         ignore_error: false
+      - cmd: ./{{.BINARY}} check testdata/rules_if_expr.yml
+        ignore_error: false
+      - cmd: ./{{.BINARY}} check --branch main testdata/rules_if_expr.yml
+        ignore_error: false
+      - cmd: ./{{.BINARY}} check --branch feat/x testdata/rules_if_expr.yml
+        ignore_error: false
       - cmd: ./{{.BINARY}} check samba-testdata/.gitlab-ci.yml
         ignore_error: false
       - cmd: ./{{.BINARY}} check samba-testdata/.gitlab-ci-coverage.yml
diff --git a/internal/cicontext/eval.go b/internal/cicontext/eval.go
index 44d5523..0e1914d 100644
--- a/internal/cicontext/eval.go
+++ b/internal/cicontext/eval.go
@@ -9,12 +9,15 @@ import (
 // variable resolver.
 //
 // Supported:
-//   - Variable references: $VAR_NAME
+//   - Variable references: $VAR_NAME or ${VAR_NAME}
 //   - String literals:     "value" or 'value'
 //   - Null keyword:        null
 //   - Comparison:          == != =~ !~
 //   - Boolean:             && || !
 //   - Grouping:            ( )
+//   - Regex flags:         /pattern/i (case-insensitive), /pattern/m, /pattern/s
+//   - Multi-line:          newlines between tokens are treated as whitespace
+//   - Variable regex RHS:  $VAR =~ $PATTERN when $PATTERN holds a /regex/ string
 //
 // Regex patterns use Go's regexp syntax, which covers the common RE2 subset
 // used by GitLab CI. Unsupported or unparseable expressions fall back to true
@@ -56,8 +59,13 @@ func (p *exprParser) consume(tok string) bool {
 }
 
 func (p *exprParser) skipWS() {
-	for p.pos < len(p.s) && (p.s[p.pos] == ' ' || p.s[p.pos] == '\t') {
-		p.pos++
+	for p.pos < len(p.s) {
+		b := p.s[p.pos]
+		if b == ' ' || b == '\t' || b == '\n' || b == '\r' {
+			p.pos++
+			continue
+		}
+		break
 	}
 }
 
@@ -67,11 +75,11 @@ func (p *exprParser) skipWS() {
 //   and_expr   → not_expr ( '&&' not_expr )*
 //   not_expr   → '!' not_expr | primary
 //   primary    → '(' or_expr ')' | comparison
-//   comparison → value ( op value | regex_op regex )? | value
-//   value      → '$' ident | '"' … '"' | "'" … "'" | 'null'
+//   comparison → value ( op value | regex_op regex_rhs )?
+//   value      → '$' '{' ident '}' | '$' ident | '"' … '"' | "'" … "'" | 'null'
 //   op         → '==' | '!='
 //   regex_op   → '=~' | '!~'
-//   regex      → '/' … '/'
+//   regex_rhs  → '/' … '/' flags? | '$' ident (where ident value is '/…/flags')
 
 func (p *exprParser) parseOr() (bool, bool) {
 	left, ok := p.parseAnd()
@@ -165,8 +173,11 @@ func (p *exprParser) parseComparison() (bool, bool) {
 
 	case p.consume("=~"):
 		p.skipWS()
-		pat, ok := p.parseRegexLiteral()
-		if !ok {
+		pat, patOk, permissive := p.parseRegexRHS()
+		if permissive {
+			return true, true
+		}
+		if !patOk {
 			return false, false
 		}
 		re, err := regexp.Compile(pat)
@@ -177,8 +188,11 @@ func (p *exprParser) parseComparison() (bool, bool) {
 
 	case p.consume("!~"):
 		p.skipWS()
-		pat, ok := p.parseRegexLiteral()
-		if !ok {
+		pat, patOk, permissive := p.parseRegexRHS()
+		if permissive {
+			return true, true
+		}
+		if !patOk {
 			return false, false
 		}
 		re, err := regexp.Compile(pat)
@@ -192,13 +206,47 @@ func (p *exprParser) parseComparison() (bool, bool) {
 	return leftStr != "", true
 }
 
-// parseValue reads $VAR, "string", 'string', or null.
+// parseRegexRHS parses the right-hand side of =~ / !~ operators.
+// Returns (pattern, ok, permissive):
+//   - /regex/flags literal  → (pattern, true, false)
+//   - $VAR whose value is /regex/flags → (pattern, true, false)
+//   - $VAR whose value is empty or not a /regex/ → ("", false, true) — caller uses permissive true
+//   - parse error → ("", false, false)
+func (p *exprParser) parseRegexRHS() (pat string, ok bool, permissive bool) {
+	if p.peek() == '/' {
+		pat, ok = p.parseRegexLiteral()
+		return pat, ok, false
+	}
+	if p.peek() == '$' {
+		varVal, varOk := p.parseValue()
+		if !varOk {
+			return "", false, false
+		}
+		pat, ok = extractRegexFromString(varVal)
+		if !ok {
+			return "", false, true // variable is not a /regex/ value → permissive
+		}
+		return pat, true, false
+	}
+	return "", false, false
+}
+
+// parseValue reads $VAR, ${VAR}, "string", 'string', or null.
 // null and undefined variables both produce an empty string.
 func (p *exprParser) parseValue() (string, bool) {
 	p.skipWS()
 
 	if p.peek() == '$' {
 		p.pos++ // consume '$'
+		if p.peek() == '{' {
+			p.pos++ // consume '{'
+			name := p.parseIdent()
+			if name == "" || p.peek() != '}' {
+				return "", false
+			}
+			p.pos++ // consume '}'
+			return p.vars(name), true
+		}
 		name := p.parseIdent()
 		if name == "" {
 			return "", false
@@ -261,7 +309,8 @@ func (p *exprParser) parseRegexLiteral() (string, bool) {
 		b := p.s[p.pos]
 		if b == '/' {
 			p.pos++ // consume closing '/'
-			return sb.String(), true
+			flags := p.parseRegexFlags()
+			return applyRegexFlags(flags, sb.String()), true
 		}
 		if b == '\\' && p.pos+1 < len(p.s) {
 			p.pos++
@@ -275,6 +324,68 @@ func (p *exprParser) parseRegexLiteral() (string, bool) {
 	return "", false // unterminated regex
 }
 
+// parseRegexFlags reads zero or more regex flag letters (i, m, s) after the
+// closing '/'. Unknown letters are consumed but ignored.
+func (p *exprParser) parseRegexFlags() string {
+	start := p.pos
+	for p.pos < len(p.s) && isIdentByte(p.s[p.pos]) {
+		p.pos++
+	}
+	return p.s[start:p.pos]
+}
+
+// applyRegexFlags prepends Go regexp flag groups to pattern (e.g. (?i) for 'i').
+// Unknown flags are silently ignored.
+func applyRegexFlags(flags, pattern string) string {
+	if flags == "" {
+		return pattern
+	}
+	var prefix strings.Builder
+	for _, f := range flags {
+		switch f {
+		case 'i':
+			prefix.WriteString("(?i)")
+		case 'm':
+			prefix.WriteString("(?m)")
+		case 's':
+			prefix.WriteString("(?s)")
+		}
+	}
+	return prefix.String() + pattern
+}
+
+// extractRegexFromString parses a /pattern/flags string (typically from a CI
+// variable) and returns a Go regexp pattern with flags applied.
+func extractRegexFromString(s string) (string, bool) {
+	s = strings.TrimSpace(s)
+	if len(s) == 0 || s[0] != '/' {
+		return "", false
+	}
+	var sb strings.Builder
+	i := 1
+	for i < len(s) {
+		b := s[i]
+		if b == '/' {
+			i++ // past closing '/'
+			var flags strings.Builder
+			for i < len(s) && isIdentByte(s[i]) {
+				flags.WriteByte(s[i])
+				i++
+			}
+			return applyRegexFlags(flags.String(), sb.String()), true
+		}
+		if b == '\\' && i+1 < len(s) {
+			i++
+			sb.WriteByte('\\')
+			sb.WriteByte(s[i])
+		} else {
+			sb.WriteByte(b)
+		}
+		i++
+	}
+	return "", false // unterminated
+}
+
 func isIdentByte(b byte) bool {
 	return (b >= 'a' && b <= 'z') || (b >= 'A' && b <= 'Z') || (b >= '0' && b <= '9') || b == '_'
 }
diff --git a/internal/cicontext/eval_test.go b/internal/cicontext/eval_test.go
index 81f40d8..f6e7d1d 100644
--- a/internal/cicontext/eval_test.go
+++ b/internal/cicontext/eval_test.go
@@ -5,10 +5,14 @@ import "testing"
 func TestEvalIf(t *testing.T) {
 	vars := func(key string) string {
 		m := map[string]string{
-			"CI_COMMIT_BRANCH": "develop",
-			"CI_COMMIT_TAG":    "",
+			"CI_COMMIT_BRANCH":  "develop",
+			"CI_COMMIT_TAG":     "",
 			"CI_PIPELINE_SOURCE": "push",
-			"DEPLOY_ENV":       "staging",
+			"DEPLOY_ENV":        "staging",
+			"BRANCH_PATTERN":    "/^dev/",
+			"BRANCH_PATTERN_CI": "/^DEV/i",
+			"EMPTY_PATTERN":     "",
+			"PLAIN_PATTERN":     "develop",
 		}
 		return m[key]
 	}
@@ -69,6 +73,36 @@ func TestEvalIf(t *testing.T) {
 		{"extra spaces", `  $CI_COMMIT_BRANCH  ==  "develop"  `, true},
 		{"tabs", "$CI_COMMIT_BRANCH\t==\t\"develop\"", true},
 
+		// ── Multi-line expressions (newlines between tokens) ──────────────────
+		{"multiline or true", "$CI_COMMIT_BRANCH == \"develop\" ||\n$CI_COMMIT_TAG != null", true},
+		{"multiline or false", "$CI_COMMIT_BRANCH == \"main\" ||\n$CI_COMMIT_TAG != null", false},
+		{"multiline and true", "$CI_COMMIT_BRANCH == \"develop\" &&\n$CI_PIPELINE_SOURCE == \"push\"", true},
+		{"multiline and false", "$CI_COMMIT_BRANCH == \"main\" &&\n$CI_PIPELINE_SOURCE == \"push\"", false},
+		{"multiline with crlf", "$CI_COMMIT_BRANCH == \"develop\" ||\r\n$CI_COMMIT_TAG != null", true},
+
+		// ── ${VAR} curly-brace syntax ─────────────────────────────────────────
+		{"curly var eq match", `${CI_COMMIT_BRANCH} == "develop"`, true},
+		{"curly var eq no match", `${CI_COMMIT_BRANCH} == "main"`, false},
+		{"curly var truthiness", `${CI_COMMIT_BRANCH}`, true},
+		{"curly var falsy", `${CI_COMMIT_TAG}`, false},
+		{"curly var neq null", `${CI_COMMIT_BRANCH} != null`, true},
+		{"curly mixed", `${CI_COMMIT_BRANCH} == "develop" && $CI_PIPELINE_SOURCE == "push"`, true},
+
+		// ── Regex flags (/pattern/i etc.) ─────────────────────────────────────
+		{"regex flag i match", `$CI_COMMIT_BRANCH =~ /^DEV/i`, true},
+		{"regex flag i no match", `$CI_COMMIT_BRANCH =~ /^MAIN/i`, false},
+		{"regex flag i not match", `$CI_COMMIT_BRANCH !~ /^MAIN/i`, true},
+		{"regex no flag case sensitive", `$CI_COMMIT_BRANCH =~ /^DEV/`, false},
+		{"regex flag i version tag", `$CI_PIPELINE_SOURCE =~ /^PUSH$/i`, true},
+
+		// ── Variable on right side of =~ ──────────────────────────────────────
+		{"var regex rhs match", `$CI_COMMIT_BRANCH =~ $BRANCH_PATTERN`, true},
+		{"var regex rhs no match", `$CI_PIPELINE_SOURCE =~ $BRANCH_PATTERN`, false},
+		{"var regex rhs ci flag match", `$CI_COMMIT_BRANCH =~ $BRANCH_PATTERN_CI`, true},
+		{"var regex rhs empty permissive", `$CI_COMMIT_BRANCH =~ $EMPTY_PATTERN`, true},
+		{"var regex rhs plain permissive", `$CI_COMMIT_BRANCH =~ $PLAIN_PATTERN`, true},
+		{"var regex rhs not match", `$CI_COMMIT_BRANCH !~ $BRANCH_PATTERN`, false},
+
 		// ── Permissive fallback ───────────────────────────────────────────────
 		{"unparseable returns true", `this is not valid syntax %%%`, true},
 		{"empty expr returns true", ``, true},
diff --git a/testdata/rules_if_expr.yml b/testdata/rules_if_expr.yml
new file mode 100644
index 0000000..661d4c1
--- /dev/null
+++ b/testdata/rules_if_expr.yml
@@ -0,0 +1,51 @@
+---
+# rules_if_expr.yml
+# Exercises the rules:if: expression evaluator for:
+#   - Multi-line block-scalar expressions (|| on next line)
+#   - ${VAR} curly-brace variable syntax
+#   - Regex flags (/pattern/i case-insensitive)
+#   - Parenthesised compound expressions
+# Expected: exits 0 (lints clean with no context).
+
+stages:
+  - build
+  - deploy
+
+variables:
+  DEPLOY_ENVIRONMENTS:
+    value: "staging"
+    description: "Target deployment environment"
+
+build:
+  stage: build
+  script: make build
+  rules:
+    # Multi-line expression: || on next line
+    - if: |
+        $CI_COMMIT_BRANCH == "main" ||
+        $CI_COMMIT_BRANCH == "develop"
+      when: on_success
+    - when: never
+
+deploy-feature:
+  stage: deploy
+  script: make deploy
+  rules:
+    # ${VAR} curly-brace syntax
+    - if: '${CI_COMMIT_BRANCH} != null && ${CI_COMMIT_TAG} == null'
+      when: manual
+    - when: never
+
+release:
+  stage: deploy
+  script: make release
+  rules:
+    # Case-insensitive regex flag
+    - if: '$CI_COMMIT_BRANCH =~ /^(main|master)$/i'
+      when: on_success
+    # Parenthesised compound with multi-line
+    - if: >-
+        ($CI_COMMIT_TAG != null) &&
+        ($CI_PIPELINE_SOURCE == "push" || $CI_PIPELINE_SOURCE == "web")
+      when: on_success
+    - when: never