diff --git a/.dscanner.ini b/.dscanner.ini
index 16b69e9228c..75f658e2797 100644
--- a/.dscanner.ini
+++ b/.dscanner.ini
@@ -91,6 +91,8 @@ allman_braces_check="enabled"
 redundant_attributes_check="enabled"
 ; Check for public declarations without a documented unittest
 has_public_example="enabled"
+; Check for asserts without an explanatory message
+assert_without_msg="skip-unittest"
 
 ; Configure which modules are checked with a specific checker
 ; Please help to extend these checks onto more Phobos modules
@@ -111,6 +113,8 @@ alias_syntax_check="-std.traits,-std.typecons"
 allman_braces_check="+disabled"
 ; Checks for confusing code in inline asm statements
 asm_style_check="-std.math"
+; Check for asserts without an explanatory message
+assert_without_msg="-etc.c.SQL_,-std.algorithm.comparison,-std.algorithm.iteration,-std.algorithm.searching,-std.algorithm.setops,-std.algorithm.sorting,-std.array,-std.bigint,-std.bitmanip,-std.concurrency,-std.container,-std.container.array,-std.container.binaryheap,-std.container.dlist,-std.container.rbtree,-std.container.slist,-std.conv,-std.csv,-std.datetime,-std.datetime.date,-std.datetime.interval,-std.datetime.systime,-std.datetime.timezone,-std.digest.digest,-std.digest.murmurhash,-std.digest.sha,-std.encoding,-std.exception,-std.experimental.allocator,-std.experimental.allocator.building_blocks.affix_allocator,-std.experimental.allocator.building_blocks.allocator_list,-std.experimental.allocator.building_blocks.bitmapped_block,-std.experimental.allocator.building_blocks.bucketizer,-std.experimental.allocator.building_blocks.free_list,-std.experimental.allocator.building_blocks.free_tree,-std.experimental.allocator.building_blocks.kernighan_ritchie,-std.experimental.allocator.building_blocks.null_allocator,-std.experimental.allocator.building_blocks.quantizer,-std.experimental.allocator.building_blocks.region,-std.experimental.allocator.building_blocks.scoped_allocator,-std.experimental.allocator.common,-std.experimental.allocator.gc_allocator,-std.experimental.allocator.mallocator,-std.experimental.allocator.mmap_allocator,-std.experimental.allocator.typed,-std.experimental.checkedint,-std.file,-std.format,-std.functional,-std.getopt,-std.internal.cstring,-std.internal.digest.sha_SSSE3,-std.internal.math.biguintcore,-std.internal.math.biguintnoasm,-std.internal.math.gammafunction,-std.internal.scopebuffer,-std.math,-std.mathspecial,-std.mmfile,-std.net.curl,-std.numeric,-std.outbuffer,-std.parallelism,-std.path,-std.process,-std.random,-std.range,-std.range.primitives,-std.regex,-std.regex.internal.backtracking,-std.regex.internal.generator,-std.regex.internal.ir,-std.regex.internal.kickstart,-std.regex.internal.parser,-std.regex.internal.thompson,-std.signals,-std.socket,-std.stdio,-std.string,-std.traits,-std.typecons,-std.uni,-std.uri,-std.utf,-std.uuid,-std.variant,-std.windows.registry,-std.xml"
 ; Checks for assignment to auto-ref function parameters
 auto_ref_assignment_check="-std.algorithm.mutation,-std.format,-std.typecons"
 ; Checks for variables that could be declared immutable
diff --git a/std/algorithm/comparison.d b/std/algorithm/comparison.d
index be4f7f89ef7..9bd57cda7c7 100644
--- a/std/algorithm/comparison.d
+++ b/std/algorithm/comparison.d
@@ -533,7 +533,7 @@ auto clamp(T1, T2, T3)(T1 val, T2 lower, T3 upper)
 in
 {
     import std.functional : greaterThan;
-    assert(!lower.greaterThan(upper));
+    assert(!lower.greaterThan(upper), "Lower can't be greater than upper.");
 }
 do
 {
@@ -732,7 +732,7 @@ Compares two ranges for equality, as defined by predicate $(D pred)
 template equal(alias pred = "a == b")
 {
     enum isEmptyRange(R) =
-        isInputRange!R && __traits(compiles, {static assert(R.empty);});
+        isInputRange!R && __traits(compiles, {static assert(R.empty, "");});
 
     enum hasFixedLength(T) = hasLength!T || isNarrowString!T;
 
diff --git a/std/algorithm/mutation.d b/std/algorithm/mutation.d
index b684f8fd79e..19039f45be0 100644
--- a/std/algorithm/mutation.d
+++ b/std/algorithm/mutation.d
@@ -257,7 +257,7 @@ if (isInputRange!InputRange && isForwardRange!ForwardRange)
         }
         else
         {
-            assert(front.empty);
+            assert(front.empty, "Expected front to be empty");
             // Left side was shorter. Let's step into the back.
             static if (is(InputRange == Take!ForwardRange))
             {
@@ -1528,7 +1528,7 @@ private InputRange2 moveAllImpl(alias moveOp, InputRange1, InputRange2)(
          && hasSlicing!InputRange2 && isRandomAccessRange!InputRange2)
     {
         auto toMove = src.length;
-        assert(toMove <= tgt.length);
+        assert(toMove <= tgt.length, "Source buffer needs to be smaller or equal to the target buffer.");
         foreach (idx; 0 .. toMove)
             moveOp(src[idx], tgt[idx]);
         return tgt[toMove .. tgt.length];
@@ -1537,7 +1537,7 @@ private InputRange2 moveAllImpl(alias moveOp, InputRange1, InputRange2)(
     {
         for (; !src.empty; src.popFront(), tgt.popFront())
         {
-            assert(!tgt.empty);
+            assert(!tgt.empty, "Source buffer needs to be smaller or equal to the target buffer.");
             moveOp(src.front, tgt.front);
         }
         return tgt;
@@ -1849,7 +1849,7 @@ if (s != SwapStrategy.stable
                 break;
         }
         // Advance to next blackout on the left
-        assert(blackouts[left].pos >= tgtPos);
+        assert(blackouts[left].pos >= tgtPos, "Next blackout on the left shouldn't appear before the target.");
         tgt.popFrontExactly(blackouts[left].pos - tgtPos);
         tgtPos = blackouts[left].pos;
 
diff --git a/std/digest/package.d b/std/digest/package.d
index 33fb5bf1202..3f3bc15f1ac 100644
--- a/std/digest/package.d
+++ b/std/digest/package.d
@@ -931,7 +931,7 @@ if (isDigest!T) : Digest
         nothrow ubyte[] finish(ubyte[] buf)
         in
         {
-            assert(buf.length >= this.length);
+            assert(buf.length >= this.length, "Given buffer is smaller than the local buffer.");
         }
         do
         {
@@ -967,7 +967,7 @@ if (isDigest!T) : Digest
             @trusted ubyte[] peek(ubyte[] buf) const
             in
             {
-                assert(buf.length >= this.length);
+                assert(buf.length >= this.length, "Given buffer is smaller than the local buffer.");
             }
             do
             {
diff --git a/std/json.d b/std/json.d
index 8ba0f05f782..9204de682ca 100644
--- a/std/json.d
+++ b/std/json.d
@@ -1166,7 +1166,7 @@ string toJSON(const ref JSONValue root, in bool pretty = false, in JSONOptions o
                     // Make sure we do UTF decoding iff we want to
                     // escape Unicode characters.
                     assert(((options & JSONOptions.escapeNonAsciiChars) != 0)
-                        == is(Char == dchar));
+                        == is(Char == dchar), "JSONOptions.escapeNonAsciiChars needs dchar strings");
 
                     with (JSONOptions) if (isControl(c) ||
                         ((options & escapeNonAsciiChars) >= escapeNonAsciiChars && c >= 0x80))
diff --git a/std/zip.d b/std/zip.d
index 762d62b483d..6b2c5f2e742 100644
--- a/std/zip.d
+++ b/std/zip.d
@@ -390,7 +390,7 @@ final class ZipArchive
             import std.zlib : crc32;
             () @trusted { de._crc32 = crc32(0, cast(void[]) de._expandedData); }();
         }
-        assert(de._compressedData.length == de._compressedSize);
+        assert(de._compressedData.length == de._compressedSize, "Archive member compressed failed.");
     }
 
     /** Delete de from the archive.
@@ -543,7 +543,7 @@ final class ZipArchive
         i += 22;
 
         // Write archive comment
-        assert(i + comment.length == data.length);
+        assert(i + comment.length == data.length, "Writing the archive comment failed.");
         _data[i .. data.length] = (cast(ubyte[]) comment)[];
 
         return cast(void[]) data;
diff --git a/std/zlib.d b/std/zlib.d
index 651b4f9d1fb..ce14f3c29fa 100644
--- a/std/zlib.d
+++ b/std/zlib.d
@@ -191,7 +191,7 @@ uint crc32(uint crc, const(void)[] buf)
 ubyte[] compress(const(void)[] srcbuf, int level)
 in
 {
-    assert(-1 <= level && level <= 9);
+    assert(-1 <= level && level <= 9, "Compression level needs to be within [-1, 9].");
 }
 do
 {
@@ -276,7 +276,7 @@ void[] uncompress(const(void)[] srcbuf, size_t destlen = 0u, int winbits = 15)
                 throw new ZlibException(err);
         }
     }
-    assert(0);
+    assert(0, "Unreachable code");
 }
 
 @system unittest
@@ -370,7 +370,7 @@ class Compress
     this(int level, HeaderFormat header = HeaderFormat.deflate)
     in
     {
-        assert(1 <= level && level <= 9);
+        assert(1 <= level && level <= 9, "Legal compression level are in [1, 9].");
     }
     do
     {
@@ -461,7 +461,8 @@ class Compress
     void[] flush(int mode = Z_FINISH)
     in
     {
-        assert(mode == Z_FINISH || mode == Z_SYNC_FLUSH || mode == Z_FULL_FLUSH);
+        assert(mode == Z_FINISH || mode == Z_SYNC_FLUSH || mode == Z_FULL_FLUSH,
+                "Mode must be either Z_FINISH, Z_SYNC_FLUSH or Z_FULL_FLUSH.");
     }
     do
     {
@@ -572,7 +573,7 @@ class UnCompress
     const(void)[] uncompress(const(void)[] buf)
     in
     {
-        assert(!done);
+        assert(!done, "Buffer has been flushed.");
     }
     do
     {
@@ -752,11 +753,11 @@ class UnCompress
     void[] flush()
     in
     {
-        assert(!done);
+        assert(!done, "Buffer has been flushed before.");
     }
     out
     {
-        assert(done);
+        assert(done, "Flushing failed.");
     }
     do
     {