diff --git a/CHANGES b/CHANGES
index 20485f0114..6c1f81ecf0 100644
--- a/CHANGES
+++ b/CHANGES
@@ -1,3 +1,13 @@
+4.2.0-dev.99 | 2021-09-03 17:36:09 +0000
+
+  * GH-1589: Avoid extracting IP-like strings from SMTP headers (Tim Wojtulewicz, Corelight)
+
+  * Minor updates to the external-testsuite scripts (Christian Kreibich, Corelight)
+
+    Delete the unused Baseline folder, remove a Bro-era name from gitignore,
+    change create-new-repo to work with a second argument that is actually
+    a URL, and tweak whitespace. Expand description in README and update the
+    explanation of OPENSSL_ENABLE_MD5_VERIFY in subdir-btest.cfg.
 
 4.2.0-dev.94 | 2021-08-31 15:58:00 +0200
 
diff --git a/VERSION b/VERSION
index 411ade6790..5c76bcd962 100644
--- a/VERSION
+++ b/VERSION
@@ -1 +1 @@
-4.2.0-dev.94
+4.2.0-dev.99
diff --git a/scripts/base/protocols/smtp/main.zeek b/scripts/base/protocols/smtp/main.zeek
index 3de3922717..fdc7a9542a 100644
--- a/scripts/base/protocols/smtp/main.zeek
+++ b/scripts/base/protocols/smtp/main.zeek
@@ -109,7 +109,7 @@ event zeek_init() &priority=5
 
 function find_address_in_smtp_header(header: string): string
 	{
-	local ips = extract_ip_addresses(header);
+	local ips = extract_ip_addresses(header, T);
 	# If there are more than one IP address found, return the second.
 	if ( |ips| > 1 )
 		return ips[1];
diff --git a/scripts/base/utils/addrs.zeek b/scripts/base/utils/addrs.zeek
index 92af26be96..9e63d1e732 100644
--- a/scripts/base/utils/addrs.zeek
+++ b/scripts/base/utils/addrs.zeek
@@ -83,8 +83,12 @@ function has_valid_octets(octets: string_vec): bool
 ##
 ## input: a string that may contain an IP address anywhere within it.
 ##
+## check_wrapping: if true, will only return IP addresses that are wrapped in matching
+## pairs of spaces, square brackets, curly braces, or parens. This can be used to avoid
+## extracting strings that look like IPs from innocuous strings, such as SMTP headers.
+##
 ## Returns: an array containing all valid IP address strings found in *input*.
-function extract_ip_addresses(input: string): string_vec
+function extract_ip_addresses(input: string, check_wrapping: bool &default=F): string_vec
 	{
 	local parts = split_string_all(input, ip_addr_regex);
 	local output: string_vec;
@@ -92,7 +96,24 @@ function extract_ip_addresses(input: string): string_vec
 	for ( i in parts )
 		{
 		if ( i % 2 == 1 && is_valid_ip(parts[i]) )
-			output += parts[i];
+			{
+			if ( ! check_wrapping )
+				{
+				output += parts[i];
+				}
+			else if ( i > 0 && i < |parts| - 1 )
+				{
+				local p1 = parts[i-1];
+				local p3 = parts[i+1];
+
+				if ( ( |p1| == 0 && |p3| == 0 ) ||
+				     ( p1[-1] == "\[" && p3[0] == "\]" ) ||
+			             ( p1[-1] == "\(" && p3[0] == "\)" ) ||
+			             ( p1[-1] == "\{" && p3[0] == "\}" ) ||
+			             ( p1[-1] == " " && p3[0] == " " ) )
+					output += parts[i];
+				}
+			}
 		}
 	return output;
 	}
diff --git a/testing/btest/Baseline/scripts.base.utils.addrs/output b/testing/btest/Baseline/scripts.base.utils.addrs/output
index 839799e18a..380efe357b 100644
--- a/testing/btest/Baseline/scripts.base.utils.addrs/output
+++ b/testing/btest/Baseline/scripts.base.utils.addrs/output
@@ -51,4 +51,13 @@ F
 ============ test extract_ip_addresses()
 [1.1.1.1, 2.2.2.2, 3.3.3.3]
 [1.1.1.1, 0:0:0:0:0:0:0:0, 3.3.3.3]
+[1.1.1.1]
+[1.1.1.1]
+[]
+[1.1.1.1]
+[1.1.1.1]
+[1.1.1.1]
+[1.1.1.1, 2.2.2.2]
+[1.1.1.1]
+[1.1.1.1]
 [6:1:2::3:4:5:6]
diff --git a/testing/btest/scripts/base/utils/addrs.test b/testing/btest/scripts/base/utils/addrs.test
index 274887fbce..6de029270c 100644
--- a/testing/btest/scripts/base/utils/addrs.test
+++ b/testing/btest/scripts/base/utils/addrs.test
@@ -135,6 +135,15 @@ event zeek_init()
 	print "============ test extract_ip_addresses()";
 	print extract_ip_addresses("this is 1.1.1.1 a test 2.2.2.2 string with ip addresses 3.3.3.3");
 	print extract_ip_addresses("this is 1.1.1.1 a test 0:0:0:0:0:0:0:0 string with ip addresses 3.3.3.3");
+	print extract_ip_addresses("text 1.1.1.1 text", T);
+	print extract_ip_addresses("text 1.1.1.1 text", F);
+	print extract_ip_addresses("text1.1.1.1text", T);
+	print extract_ip_addresses("text1.1.1.1text", F);
+	print extract_ip_addresses("text[1.1.1.1]text", T);
+	print extract_ip_addresses("text[1.1.1.1]text", F);
+	print extract_ip_addresses("[1.1.1.1] [2.2.2.2]", T);
+	print extract_ip_addresses("1.1.1.1", T);
+	print extract_ip_addresses("1.1.1.1", F);
 
 	# This will use the leading 6 from "IPv6" (maybe that's not intended
 	# by a person trying to parse such a string, but that's just what's going
diff --git a/testing/external/commit-hash.zeek-testing-private b/testing/external/commit-hash.zeek-testing-private
index cacb4cffe1..c2bef97a74 100644
--- a/testing/external/commit-hash.zeek-testing-private
+++ b/testing/external/commit-hash.zeek-testing-private
@@ -1 +1 @@
-b33b7c939df51317595039ed408838712b738bbb
+4b88837c49ade5d9fd980d5e6cf02ec91d19a3bb