diff --git a/data/botPolicies.json b/data/botPolicies.json
index dad04e8..160bbf0 100644
--- a/data/botPolicies.json
+++ b/data/botPolicies.json
@@ -41,7 +41,7 @@
     },
     {
       "name": "generic-browser",
-      "user_agent_regex": "Mozilla|Opera\n",
+      "user_agent_regex": "Mozilla|Opera",
       "action": "CHALLENGE"
     }
   ],
diff --git a/data/botPolicies.yaml b/data/botPolicies.yaml
index 585be15..51af499 100644
--- a/data/botPolicies.yaml
+++ b/data/botPolicies.yaml
@@ -43,7 +43,7 @@ bots:
 
 # Generic catchall rule
 - name: generic-browser
-  user_agent_regex: >
+  user_agent_regex: >-
     Mozilla|Opera
   action: CHALLENGE
 
diff --git a/data/bots/ai-robots-txt.yaml b/data/bots/ai-robots-txt.yaml
index 19cbe93..ef2790c 100644
--- a/data/bots/ai-robots-txt.yaml
+++ b/data/bots/ai-robots-txt.yaml
@@ -1,4 +1,4 @@
 - name: "ai-robots-txt"
-  user_agent_regex: >
+  user_agent_regex: >-
     AI2Bot|Ai2Bot-Dolma|Amazonbot|anthropic-ai|Applebot|Applebot-Extended|Brightbot 1.0|Bytespider|CCBot|ChatGPT-User|Claude-Web|ClaudeBot|cohere-ai|cohere-training-data-crawler|Crawlspace|Diffbot|DuckAssistBot|FacebookBot|FriendlyCrawler|Google-Extended|GoogleOther|GoogleOther-Image|GoogleOther-Video|GPTBot|iaskspider/2.0|ICC-Crawler|ImagesiftBot|img2dataset|ISSCyberRiskCrawler|Kangaroo Bot|Meta-ExternalAgent|Meta-ExternalFetcher|OAI-SearchBot|omgili|omgilibot|PanguBot|Perplexity-User|PerplexityBot|PetalBot|Scrapy|SemrushBot-OCOB|SemrushBot-SWA|Sidetrade indexer bot|Timpibot|VelenPublicWebCrawler|Webzio-Extended|YouBot
   action: DENY
\ No newline at end of file
diff --git a/docs/docs/CHANGELOG.md b/docs/docs/CHANGELOG.md
index bedd38e..2e7c311 100644
--- a/docs/docs/CHANGELOG.md
+++ b/docs/docs/CHANGELOG.md
@@ -11,6 +11,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+- Ensure regexes can't end in newlines ([#372](https://github.com/TecharoHQ/anubis/issues/372))
 - Add documentation for default allow behavior (implicit rule)
 - Enable [importing configuration snippets](./admin/configuration/import.mdx) ([#321](https://github.com/TecharoHQ/anubis/pull/321))
 - Refactor check logic to be more generic and work on a Checker type
diff --git a/lib/policy/checker.go b/lib/policy/checker.go
index ad98ced..51223cd 100644
--- a/lib/policy/checker.go
+++ b/lib/policy/checker.go
@@ -110,11 +110,11 @@ func NewUserAgentChecker(rexStr string) (Checker, error) {
 }
 
 func NewHeaderMatchesChecker(header, rexStr string) (Checker, error) {
-	rex, err := regexp.Compile(rexStr)
+	rex, err := regexp.Compile(strings.TrimSpace(rexStr))
 	if err != nil {
 		return nil, fmt.Errorf("%w: regex %s failed parse: %w", ErrMisconfiguration, rexStr, err)
 	}
-	return &HeaderMatchesChecker{header, rex, internal.SHA256sum(header + ": " + rexStr)}, nil
+	return &HeaderMatchesChecker{strings.TrimSpace(header), rex, internal.SHA256sum(header + ": " + rexStr)}, nil
 }
 
 func (hmc *HeaderMatchesChecker) Check(r *http.Request) (bool, error) {
@@ -135,7 +135,7 @@ type PathChecker struct {
 }
 
 func NewPathChecker(rexStr string) (Checker, error) {
-	rex, err := regexp.Compile(rexStr)
+	rex, err := regexp.Compile(strings.TrimSpace(rexStr))
 	if err != nil {
 		return nil, fmt.Errorf("%w: regex %s failed parse: %w", ErrMisconfiguration, rexStr, err)
 	}
@@ -155,7 +155,7 @@ func (pc *PathChecker) Hash() string {
 }
 
 func NewHeaderExistsChecker(key string) Checker {
-	return headerExistsChecker{key}
+	return headerExistsChecker{strings.TrimSpace(key)}
 }
 
 type headerExistsChecker struct {
@@ -180,11 +180,11 @@ func NewHeadersChecker(headermap map[string]string) (Checker, error) {
 
 	for key, rexStr := range headermap {
 		if rexStr == ".*" {
-			result = append(result, headerExistsChecker{key})
+			result = append(result, headerExistsChecker{strings.TrimSpace(key)})
 			continue
 		}
 
-		rex, err := regexp.Compile(rexStr)
+		rex, err := regexp.Compile(strings.TrimSpace(rexStr))
 		if err != nil {
 			errs = append(errs, fmt.Errorf("while compiling header %s regex %s: %w", key, rexStr, err))
 			continue
diff --git a/lib/policy/config/config.go b/lib/policy/config/config.go
index 627e9cf..c670bac 100644
--- a/lib/policy/config/config.go
+++ b/lib/policy/config/config.go
@@ -24,6 +24,7 @@ var (
 	ErrInvalidPathRegex                  = errors.New("config.Bot: invalid path regex")
 	ErrInvalidHeadersRegex               = errors.New("config.Bot: invalid headers regex")
 	ErrInvalidCIDR                       = errors.New("config.Bot: invalid CIDR")
+	ErrRegexEndsWithNewline              = errors.New("config.Bot: regular expression ends with newline (try >- instead of > in yaml)")
 	ErrInvalidImportStatement            = errors.New("config.ImportStatement: invalid source file")
 	ErrCantSetBotAndImportValuesAtOnce   = errors.New("config.BotOrImport: can't set bot rules and import values at the same time")
 	ErrMustSetBotOrImportRules           = errors.New("config.BotOrImport: rule definition is invalid, you must set either bot rules or an import statement, not both")
@@ -91,12 +92,20 @@ func (b BotConfig) Valid() error {
 	}
 
 	if b.UserAgentRegex != nil {
+		if strings.HasSuffix(*b.UserAgentRegex, "\n") {
+			errs = append(errs, fmt.Errorf("%w: user agent regex: %q", ErrRegexEndsWithNewline, *b.UserAgentRegex))
+		}
+
 		if _, err := regexp.Compile(*b.UserAgentRegex); err != nil {
 			errs = append(errs, ErrInvalidUserAgentRegex, err)
 		}
 	}
 
 	if b.PathRegex != nil {
+		if strings.HasSuffix(*b.PathRegex, "\n") {
+			errs = append(errs, fmt.Errorf("%w: path regex: %q", ErrRegexEndsWithNewline, *b.PathRegex))
+		}
+
 		if _, err := regexp.Compile(*b.PathRegex); err != nil {
 			errs = append(errs, ErrInvalidPathRegex, err)
 		}
@@ -108,6 +117,10 @@ func (b BotConfig) Valid() error {
 				continue
 			}
 
+			if strings.HasSuffix(expr, "\n") {
+				errs = append(errs, fmt.Errorf("%w: header %s regex: %q", ErrRegexEndsWithNewline, name, expr))
+			}
+
 			if _, err := regexp.Compile(expr); err != nil {
 				errs = append(errs, ErrInvalidHeadersRegex, err)
 			}
diff --git a/lib/policy/config/testdata/bad/regex_ends_newline.json b/lib/policy/config/testdata/bad/regex_ends_newline.json
new file mode 100644
index 0000000..14c7fa9
--- /dev/null
+++ b/lib/policy/config/testdata/bad/regex_ends_newline.json
@@ -0,0 +1,21 @@
+{
+  "bots": [
+    {
+      "name": "user-agent-ends-newline",
+      "user_agent_regex": "Mozilla\n",
+      "action": "CHALLENGE"
+    },
+    {
+      "name": "path-ends-newline",
+      "path_regex": "^/evil/.*$\n",
+      "action": "CHALLENGE"
+    },
+    {
+      "name": "headers-ends-newline",
+      "headers_regex": {
+        "CF-Worker": ".*\n"
+      },
+      "action": "CHALLENGE"
+    }
+  ]
+}
diff --git a/lib/policy/config/testdata/bad/regex_ends_newline.yaml b/lib/policy/config/testdata/bad/regex_ends_newline.yaml
new file mode 100644
index 0000000..1f0ae85
--- /dev/null
+++ b/lib/policy/config/testdata/bad/regex_ends_newline.yaml
@@ -0,0 +1,17 @@
+bots:
+- name: user-agent-ends-newline
+  # Subtle bug: this ends with a newline
+  user_agent_regex: >
+    Mozilla
+  action: CHALLENGE
+- name: path-ends-newline
+  # Subtle bug: this ends with a newline
+  path_regex: >
+    ^/evil/.*$
+  action: CHALLENGE
+- name: headers-ends-newline
+  # Subtle bug: this ends with a newline
+  headers_regex:
+    CF-Worker: >
+      .*
+  action: CHALLENGE
\ No newline at end of file